[ CAS No. 23012-14-8 ] {[proInfo.proName]}

Name: 23012-14-8|Ethyl oxazole-4-carboxylate|97%
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Quality Control of [ 23012-14-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 23012-14-8 ]

Product Details of [ 23012-14-8 ]

CAS No. :	23012-14-8	MDL No. :	MFCD04114940
Formula :	C₆H₇NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UBESIXFCSFYQNK-UHFFFAOYSA-N
M.W :	141.13	Pubchem ID :	2763217
Synonyms :

Calculated chemistry of [ 23012-14-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.59
TPSA :	52.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	-0.43
Log Po/w (SILICOS-IT) :	0.94
Consensus Log Po/w :	0.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.45
Solubility :	5.03 mg/ml ; 0.0357 mol/l
Class :	Very soluble
Log S (Ali) :	-1.57
Solubility :	3.77 mg/ml ; 0.0267 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.69
Solubility :	2.86 mg/ml ; 0.0203 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.25

Safety of [ 23012-14-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23012-14-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 23012-14-8 ]
Downstream synthetic route of [ 23012-14-8 ]

[ 23012-14-8 ] Synthesis Path-Upstream 1~9

1
[ 23012-14-8 ]
[ 23012-13-7 ]

Reference： [1] Heterocycles, 2000, vol. 53, # 5, p. 1167 - 1170
[2] Journal of the Chemical Society, 1947, p. 96,100
[3] Journal of Organic Chemistry, 1999, vol. 64, # 13, p. 4995 - 4998

2
[ 2949-22-6 ]
[ 23012-14-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With formic acid In tetrahydrofuran for 0.5 h; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 1 h; Heating / reflux	To a sol. of formic acid (8.62 mL, 228 mmol) in dry THF (200 mL) was added portionwise CDI (37.05 g, 228 mmol), whereas a gas evolution occurred. The mixture was stirred for 30 min, and a sol. of ethyl isocyanoacetate (25 mL, 228 mmol) in Et3N (60.5 mL, 434mmol) was added to the reaction mixture. The mixture was stirred at rt for 1 h, then under reflux overnight. The reaction mixture was allowed to cool to rt. Water was added, and the mixture was extracted with Et2O (3x). The combined org. extracts were dried over MgSO4, filtered and concentrated. Purification of the residue by FC (EtOAc / heptane; 1:5 -> 1:3 - 1:1) yielded the title compound (27.2 g, 84percent). LC-MS: t_R = 0.58, ES+: 142.07.

Reference： [1] Patent: WO2006/21402, 2006, A1, . Location in patent: Page/Page column 33-34

3
[ 64-18-6 ]
[ 2999-46-4 ]
[ 23012-14-8 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 19, p. 6027 - 6032
[2] Liebigs Annalen der Chemie, 1979, p. 1370 - 1387
[3] Patent: US2009/170907, 2009, A1, . Location in patent: Page/Page column 47

4
[ 10535-67-8 ]
[ 2999-46-4 ]
[ 23012-14-8 ]

Reference： [1] Heterocycles, 2012, vol. 86, # 2, p. 1003 - 1008

5
[ 2999-46-4 ]
[ 530-62-1 ]
[ 23012-14-8 ]

Reference： [1] Heterocycles, 2000, vol. 53, # 5, p. 1167 - 1170

6
[ 3154-51-6 ]
[ 23012-14-8 ]

Reference： [1] Liebigs Annalen der Chemie, 1979, p. 1370 - 1387

7
[ 23012-14-8 ]
[ 74-88-4 ]
[ 10200-43-8 ]

Reference： [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 4, p. 647 - 650

8
[ 23012-14-8 ]
[ 23012-15-9 ]

Reference： [1] Heterocycles, 2012, vol. 86, # 2, p. 1003 - 1008
[2] Helvetica Chimica Acta, 1960, vol. 43, p. 1522 - 1530

9
[ 23012-14-8 ]
[ 118994-84-6 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2222 - 2229
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 3, p. 647 - 654
[3] Organic Letters, 2007, vol. 9, # 10, p. 1875 - 1878
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 2928 - 2930

[ 23012-14-8 ] Synthesis Path-Downstream 1~88

1
[ 23012-14-8 ]
[ 23012-13-7 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 1167 - 1170
[2]Journal of the Chemical Society,1947,p. 96,100
[3]Journal of Organic Chemistry,1999,vol. 64,p. 4995 - 4998

2
[ 23012-14-8 ]
[ 23012-15-9 ]

Reference： [1]Heterocycles,2012,vol. 86,p. 1003 - 1008
[2]Helvetica Chimica Acta,1960,vol. 43,p. 1522 - 1530

3
[ 23012-14-8 ]
[ 155742-48-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With methanol; lithium borohydride; at 0 - 25℃; for 2h;Inert atmosphere;	(1) Add 6.8 g of ethyl 4-oxazolecarboxylate (A-1b) and 204 ml of methanol to the reaction vessel, cool to 0 C, add 1.7g of lithium borohydride, replace with nitrogen, stir at 25 C for 2 hours, and react The solution was quenched with water, concentrated to remove the organic solvent, and the residue was extracted with dichloromethane. The organic phase was washed, dried, and filtered.The filtrate was concentrated and purified by column chromatography to obtain 4-hydroxymethyloxazole compound (A-2b) (4.6 g of pale yellow oil, yield 95%);
72%	With lithium triethylborohydride; In tetrahydrofuran; at -78 - 20℃; for 0.166667h;	To a sol. oxazole-4-carboxylic acid ethyl ester (26.66 g, 189 mmol) in THF (550 mL) was added dropwise at -78 C LiBHEt3 (1M in THF, 341 mL, 341 mmol). When the addition was complete, the mixture was stirred for 10 min at -78 C, then was allowed to warm to rt. When the reaction mixture had reached rt, it was concentrated under reduced pressure and was diluted with Et2O. The mixture was washed with little water. The org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 99:1 -> 97:3 -> 95:5 -> 93:7) yielded the title compound (13.5 g, 72%). LC-MS: tR = 0.20, ES+: 141.08.
56%		To a solution of ethyl oxazole-4-carboxylate (1.0 g, 7.1 mmol) in THF (20 mL) was added LAH (330 mg, 8.5 mmol) portion wise at 0 C. After stirring at 0 C for 30 mi H20 (0.3 mL), 15% NaOH (0.3 mL) and H20 (0.9 mL) were then added dropwise at 0 C. The mixture was stirred at room temperature for another 20 mm, dried over MgSO4 and filtered. The filtrate was concentrated to give oxazol-4-ylmethanol (390 mg, yield: 56%) as yellow oil. ?H NIVIR (300 IVIHz, CDC13): oe = 7.90 (s, 1H), 7.64 (d, J= 0.3 Hz, 1H), 4.63 (s, 2H).

56%	With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 - 25℃; for 72h;	Step 1 : Preparation of oxazol-4-ylmethanol. [0743] To a solution of ethyl oxazole-4-carboxylate (2.00 g, 14.2 mmol in THF (20 mL)/H20 (3 mL) was added NaBFL (1.07 g, 28.3 mmol) at 0 C and then the mixture was stirred at 25 C for 72 h. A white cloudy was formed. To the mixture was added anhydrous Na2S04 (20 g) and the mixture was stirred at 25 C for 1 hour. The mixture was filtered and the cake was washed with MTBE (20 mL). The combined organic layer was concentrated to dryness. The residue was purified by Combi Flash (EtOAc in pentane from 10% to 100%) to give oxazol-4-ylmethanol (800 mg, 56% yield) as colorless oil. NMR (400 MHz, CDCh) d 2.52 (1H, brt, J= 5.6 Hz), 4.64 (2H, d, J = 5.6 Hz), 7.64 (1H, d, J= 0.8 Hz), 7.89 (1H, s).
27%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 0℃; for 3h;	Reference Example 29; 1,3-Oxazol-4-ylmethanol; To a suspension of lithium aluminum hydride (2.69 g, 70:9 mmol) in tetrahydrofuran (50 ml) was added dropwise a solution of ethyl 1,3-oxazole-4-carboxylate (5.00 g, 35.4 mmol) in tetrahydrofuran .(50 ml) at-78C. The reaction.mixture was stirred at the same temperature for 2 hrs, and the temperature was gradually raised to 0C. After stirring for 1 hr, water (2.7 ml) was added, then 15% aqueous sodium hydroxide solution (2.7 ml) and then water (8.1 ml) were added and the mixture was stirred. The reaction mixture was dried over anhydrous MgS04, the precipitate was filtered off through celite, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate to give the title compound (930 mg, 27%) as a colorless oil. ¹H-NMR (CDCl3) No.: 3.27 (lH, br s), 4.64 (2H, s), 7.64 (lH, s) , 7.90 (lH, s).
	With diisobutylaluminium hydride; In tetrahydrofuran; hexanes; at -78 - 0℃;	B. 1,3-Oxazol-4-ylmethanol To a solution of ethyl 1,3-oxazole-4-carboxylate (0.178 g, 1.26 mmol) in anhydrous THF (5 mL) at -78 C. was added DIBAL-H (2.52 mL of a 1.0 M solution in hexanes, 2.52 mmol), dropwise over 3 min. After 1 h, the cooling bath was removed, and the solution warmed to 0 C. After stirring 2.5 h at 0 C., the reaction was quenched with MeOH, MgSO4 (ca. 0.3 g) was added and the mixture stirred 30 min. The whole mixture was filtered through Celite (EtOAc wash), concentrated in vacuo and allowed to stand at rt over night. The residue was slurried in EtOAc and filtered again through Celite. The filtrate was concentrated in vacuo, affording 0.103 g of the title compound as a pale yellow oil which was used without further purification: 1H NMR (400 MHz, CDCl3) delta 7.90 (s, 1H), 7.64 (app. q, J=0.9 Hz, 1H), 4.64 (d, J=6.0 Hz, 2H), 3.40 (t, J=6.1 Hz, 1H).
		PREPARATION 77; Oxazol-4-yl-methanol; DIBAL-H (56 ml of a 1.0 M solution in toluene) was added drop-wise over 15 minutes to a solution of oxazole-4-carboxylic acid ethyl ester (7.50 g, 53.1 mmol) in THF (140 ml) at -78 C. The resulting solution was stirred at -78 C. for 30 min and then further DIBAL-H (56 mL of a 1.0 M solution in toluene, 56.0 mmol) was added over 15 minutes. The reaction was then left to slowly warm from -78 C. to room temperature for 16 hours. The resulting bright yellow solution was cooled to 0 C. in an ice bath and Na2SO4.10 H2O (15.9 g-equal weight to DIBAL-H added) was added in small portions (CARE-slow addition to prevent exotherm) to cause precipitation of aluminium salts. The mixture was left to warm to room temperature and after stirring for 90 mins the resulting suspension was filtered through a layer of celite. The celite plug was rinsed with dichloromethane (3×100 mL) and methanol (2×100 mL) and the filtrates were combined. The solvent was removed under reduced pressure, providing the title compound (4.8 g) as a brown oil.1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.60 (s, 2 H), 7.6 (s, 1 H), 7.9 (s, 1 H)

Reference： [1]Patent: CN110526878,2019,A .Location in patent: Paragraph 0127; 0128
[2]Synlett,1998,p. 1022 - 1024
[3]Patent: WO2006/21402,2006,A1 .Location in patent: Page/Page column 34
[4]Patent: WO2018/132372,2018,A1 .Location in patent: Paragraph 00369
[5]Patent: WO2019/126731,2019,A1 .Location in patent: Paragraph 0743
[6]Patent: WO2005/105802,2005,A1 .Location in patent: Page/Page column 109
[7]Patent: US2009/170907,2009,A1 .Location in patent: Page/Page column 47
[8]Patent: US2007/197478,2007,A1 .Location in patent: Page/Page column 57
[9]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3459 - 3468

4
[ 23012-14-8 ]
[ 591-50-4 ]
[ 39819-39-1 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1684 - 1687
[2]Tetrahedron Letters,2005,vol. 46,p. 8573 - 8577

5
[ 23012-14-8 ]
[ 591-50-4 ]
[ 39819-39-1 ]
[ 93729-29-4 ]
[ 32998-97-3 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 2053 - 2063
[2]Tetrahedron Letters,2005,vol. 46,p. 8573 - 8577
[3]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463
[4]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463

6
[ 23012-14-8 ]
[ 118994-84-6 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2222 - 2229
[2]European Journal of Organic Chemistry,2015,vol. 2015,p. 647 - 654
[3]Organic Letters,2007,vol. 9,p. 1875 - 1878
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2928 - 2930

7
[ 3154-51-6 ]
[ 23012-14-8 ]

Reference： [1]Liebigs Annalen der Chemie,1979,p. 1370 - 1387

8
[ 23012-14-8 ]
5-bromo-1,3-oxazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide;1,1'-azobis (cyclohexanecarbonitrile); In tetrachloromethane;	Bromination of compound 22 with one equivalent of N-bromosuccinimide in the presence of 1,1'-azobis(cyclohexanecarbonitrile) in CCl4 gives the corresponding 5-bromo derivative (compound 23). It has been found (53-55) that the nuclear bromination of oxazoles either with bromine or with N-bromosuccinimide occurs preferentially at C-5; if this position is occupied, then at C-4, but not at C-2. Selective ammonolysis of compound 23 with methanolic ammonia (saturated at 0 C.) at controlled temperature yields 5-bromo-1,3-oxazole-4-carboxamide (compound 24).

Reference： [1]Patent: US6069132,2000,A

9
[ 2949-22-6 ]
[ 23012-14-8 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a sol. of formic acid (8.62 mL, 228 mmol) in dry THF (200 mL) was added portionwise CDI (37.05 g, 228 mmol), whereas a gas evolution occurred. The mixture was stirred for 30 min, and a sol. of ethyl isocyanoacetate (25 mL, 228 mmol) in Et3N (60.5 mL, 434mmol) was added to the reaction mixture. The mixture was stirred at rt for 1 h, then under reflux overnight. The reaction mixture was allowed to cool to rt. Water was added, and the mixture was extracted with Et2O (3x). The combined org. extracts were dried over MgSO4, filtered and concentrated. Purification of the residue by FC (EtOAc / heptane; 1:5 -> 1:3 - 1:1) yielded the title compound (27.2 g, 84%). LC-MS: tR = 0.58, ES+: 142.07.

Reference： [1]Patent: WO2006/21402,2006,A1 .Location in patent: Page/Page column 33-34

10
[ 96-43-5 ]
[ 23012-14-8 ]
[ 54679-18-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

11
[ 3437-95-4 ]
[ 23012-14-8 ]
[ 54679-18-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

12
[ 3034-52-4 ]
[ 23012-14-8 ]
[ 1055195-13-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

13
[ 3034-53-5 ]
[ 23012-14-8 ]
[ 1055195-13-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

14
[ 626-60-8 ]
[ 23012-14-8 ]
[ 1014630-47-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[2]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463

15
[ 109-09-1 ]
[ 23012-14-8 ]
[ 460081-26-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[2]Green Chemistry,2010,vol. 12,p. 2053 - 2063

16
[ 109-04-6 ]
[ 23012-14-8 ]
[ 460081-26-9 ]

Yield	Reaction Conditions	Operation in experiment
0.3 g	With caesium carbonate; tris-(o-tolyl)phosphine; In 1,4-dioxane; water; at 80℃; for 2h;Inert atmosphere;	To a stirred suspenstion of 2-bromopyridine (500 mg, 3.1847 mol, leq), <strong>[23012-14-8]ethyl oxazole-4-carboxylate</strong> (500 mg, 3.184 mmol, leq), CS2CO3 (2.5e q, 2.59 gm, 7.96 mmol) in dioxane (10 mL) and water (2 mL) was purged with nitrogen for 5 minutes. P(o-tolyl)3 (193.6 mg, 0.63 mmol, 0.2 eq) was added to the reaction mixture, which was heated to 80 C for 2 hours. The cooled reaction mixture was diluted with water, and then extracted with EtOAc. The combined EtOAc extracts was washed with water, dried over Na2S04, filtered through pad of silica gel and concentrated. The residue was purified by using silica gel (eluting with 5-40% EtO Ac/hexanes) to give ethyl 2-(pyri din-2 -yl)oxazole-4-carboxylate (0.3 g). LCMS: 220 [M+H] +.

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[3]Organic Letters,2011,vol. 13,p. 3082 - 3085
[4]Patent: WO2019/195810,2019,A2 .Location in patent: Paragraph 0490

17
[ 5029-67-4 ]
[ 23012-14-8 ]
[ 460081-26-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[2]Organic Letters,2018,vol. 20,p. 1684 - 1687

18
[ 626-55-1 ]
[ 23012-14-8 ]
[ 1014630-47-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

19
[ 1120-90-7 ]
[ 23012-14-8 ]
[ 1014630-47-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

20
[ 623-03-0 ]
[ 23012-14-8 ]
[ 1055195-11-3 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463
[2]Green Chemistry,2010,vol. 12,p. 2053 - 2063
[3]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

21
[ 5332-24-1 ]
[ 23012-14-8 ]
[ 1055195-14-6 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[3]Green Chemistry,2010,vol. 12,p. 2053 - 2063
[4]Organic Letters,2011,vol. 13,p. 3082 - 3085

22
[ 23012-14-8 ]
[ 591-50-4 ]
[ 39819-39-1 ]
[ 93729-29-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

23
[ 23012-14-8 ]
[ 623-12-1 ]
[ 78979-61-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

24
[ 23012-14-8 ]
[ 696-62-8 ]
[ 1055195-16-8 ]
[ 78979-61-0 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 2053 - 2063
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[3]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463

25
[ 23012-14-8 ]
[ 3058-39-7 ]
[ 1055195-11-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[2]Organic Letters,2018,vol. 20,p. 1684 - 1687

26
[ 23012-14-8 ]
[ 104-88-1 ]
[ 1055195-12-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

27
[ 23012-14-8 ]
[ 1122-91-4 ]
[ 1055195-12-4 ]
[ 1055195-15-7 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

28
[ 23012-14-8 ]
[ 108-90-7 ]
[ 39819-39-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; caesium carbonate; CyJohnPhos; In 1,4-dioxane; at 110℃; for 18h;Inert atmosphere;	General procedure: Oxazole or thiazole-4-carboxylate derivative (0.35mmol or 0.27mmol) was placed in a dried-oven sealed tub (10ml) containing a magnetic stir bar with Pd(OAc)2 (5mol%), ligand (10mol%) and carbonate base (2equiv). A solution of halide (1equiv) in dry dioxane or DMF (1ml) was added. The resulting mixture was purged with nitrogen and stirred at 110C for 18h. After filtration on Celite and concentration under vacuo, the crude product was purified by flash column chromatography on silica gel using a mixture of petroleum ether-Ethyl acetate as eluent to give pure arylated products 1b-d and 2b-d.

Reference： [1]Tetrahedron,2013,vol. 69,p. 4375 - 4380
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386

29
[ 23012-14-8 ]
[ 540-37-4 ]
[ 391248-21-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7383 - 7386
[2]Chemistry - A European Journal,2011,vol. 17,p. 14450 - 14463

30
[ 109-65-9 ]
[ 23012-14-8 ]
[ 1134024-20-6 ]

Yield	Reaction Conditions	Operation in experiment
0.19 g	With palladium diacetate; caesium carbonate; CyJohnPhos; In tetrahydrofuran; at 110℃; for 18h;Inert atmosphere;	Reference Production Example 302 (0945) Palladium acetate (28 mg, 0.13 mmol), (2-biphenyl)dicyclohexylphosphine (88 mg, 0.25 mmol) and cesium carbonate (1.63 g, 5.0 mmol) were added to tetrahydrofuran (7 mL). Ethyl oxazole-4-carboxylate (0.35 g, 2.5 mmol) and 1-bromobutane (0.69 g, 5.0 mmol) were added to the mixed liquid at room temperature. The air in the reaction vessel was replaced with nitrogen, and then the mixture was stirred at 110C for 18 hours. Water was added to the reaction mixture, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.19 g of ethyl 2-butyl-oxazole-4-carboxylate represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)) :0.93(3H, t), 1.33-1.43(5H, m), 1.72-1.81(2H, m), 2.82(2H, t), 4.39(2H, q), 8.14(1H, s)

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 647 - 650
[2]Patent: EP2952096,2015,A1 .Location in patent: Paragraph 0945

31
[ 23012-14-8 ]
[ 1362690-82-1 ]
[ 1134024-31-9 ]