1475-11-2|1-(3,4-Dichlorophenyl)ethanol| Ambeed

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Quality Control of [ 1475-11-2 ] Purity: 95% SDS Specification

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Product Details of [ 1475-11-2 ]

CAS No. :	1475-11-2
Formula :	C₈H₈Cl₂O
M.W :	191.06
SMILES Code :	CC(O)C1=CC=C(Cl)C(Cl)=C1
MDL No. :	MFCD00021865
Boiling Point :	No data available
InChI Key :	VZTGSONNNMGQNQ-UHFFFAOYSA-N
Pubchem ID :	97899

Safety of [ 1475-11-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H318-H335-H410
Precautionary Statements:	P261-P273-P280-P305+P351+P338
Class:	9
UN#:	3082
Packing Group:	Ⅲ

Computational Chemistry of [ 1475-11-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	47.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.29
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.72
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.03
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.89

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.45
Solubility	0.0672 mg/ml ; 0.000352 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.42
Solubility	0.0724 mg/ml ; 0.000379 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.49
Solubility	0.0614 mg/ml ; 0.000321 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.11 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.8

Application In Synthesis of [ 1475-11-2 ]

* 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.

Downstream synthetic route of [ 1475-11-2 ]

[ 1475-11-2 ] Synthesis Path-Downstream 1~34

1
[ 1475-11-2 ]
[ 2642-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; silica gel; In acetonitrile; at 70℃; for 8h;Molecular sieve;	General procedure: The above secondary alcohol was dissolved in acetonitrile (30mL). Molecular sieve (1.5g), silica gel (1.5g) and activated MnO2 (3.5g, 40mmol) were added, and the mixture was stirred at 70C for 8h. upon completion of the oxidation, the resulting suspension was filtered through diatomite, and the filtrate was concentrated by rotary evaporation. Purification of the residue by column chromatography (petroleum ethrt/EtOAc, 15:1) afforded ketone 13.

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1741 - 1746.
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3466 - 3471.
[3]Arkiv foer Kemi,1955,vol. 7,p. 577,578.
[4]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1996 - 2000.
[5]European Journal of Medicinal Chemistry,2018,vol. 159,p. 90 - 103.

2
[ 917-64-6 ]
[ 6287-38-3 ]
[ 1475-11-2 ]

References: [1]Organic Syntheses,1955,vol. Coll. Vol. III,p. 200.

3
[ 555-31-7 ]
[ 2642-63-9 ]
[ 1475-11-2 ]

References: [1]Journal of the American Chemical Society,1944,vol. 66,p. 1295,1297.

4
[ 1475-11-2 ]
[ 2039-83-0 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3905 - 3914.

5
[ 2642-63-9 ]
[ 1475-11-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol; at 82℃; for 6h;Inert atmosphere; Green chemistry;	The 3, 4 - dichloro ethanone (189 mg, 1.0 mmol), cat. [Ir] (1.1 mg, 0 . 002 mmol, 0.2 muM %) and isopropyl alcohol (5 ml) are added to the 25 ml Kjeldahl tube, N2Protection, 82 C reaction 6 h. Cooling to room temperature, rotary evaporation to remove the solvent, then through the column chromatography (developing solvent: petroleum ether/ethyl acetate) to obtain the pure target compound, yield: 97%
94%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); hydrogen; In tert-Amyl alcohol; at 30℃; under 760.051 Torr; for 12h;Green chemistry;	General procedure: To an oven-dried 5 mL round-bottom flask were added ketone (1 mmol), cat. 7 (2.7 mg, 0.5 mol %) and tert-amyl alcohol (1 mL). Next, vacuum was applied to the flask followed by filling with H2 gas and keeping the flask attached to a balloon filled with H2 gas. The mixture was heated at 30 C for 12 h. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The alcohols were isolated and purified by filtering a hexanes/ethyl acetate (5:1) solution of the crude product through a pad of silica gel, and then removing the solvent under reduced pressure. The conversion and purity of the alcohol products was assessed using NMR spectroscopy.
80%	With sodium tetrahydroborate; ethanol; at 20℃;Cooling with ice;	2.2 mmol NaBH4 was added to 2.1 mmol of 8a in dry ethanol (10 mL) stirred in an ice bath.The suspension was further stirred at room temperature overnight. After the reaction was completed, it was quenched by the addition of 1.0 N HCl, and the remaining ethanol was evaporated under reduced pressure. The product was extracted with diethyl ether (25 mL x 2),washed with sodium bicarbonate (15 mL), and water (10 mL), dried over MgSO4, and evaporated under reduced pressure. Silica gel column chromatography (hex ane:ethyl acetate4:1) was performed to give the corresponding rac-8b. 9a-11a and 13a (2.21 mmol~2.66 mmol) were also reduced similarly. The 1H-NMR spectra of alcohols 8b [1], 9b-11b [2], and 13b [3] were in agreement with those reported in the literature. 1.2.1 1-(3?,4?-Dichlorophenyl)ethanol, rac-8b. 0.42 g (2.21 mmol) of 8a was converted to 0.34 g of rac-8b (1.77 mmol, 80%, colorless oil). 1H-NMR (400 MHz, CDCl3, 25C, TMS): delta=7.47-7.48 (m, 1H), 7.41(d, J=8.4 Hz, 1H), 7.20 (dd, J=8.4 Hz, 2.0Hz, 1H), 4.85-4.90 (m, 1H), 1.85 (brd,J=3.6 Hz, 1H), 1.48 (d, J=6.4 Hz, 3H).

	With sodium tetrahydroborate; In methanol; at 0 - 20℃;	To a stirred solution of 3,4-dichloroacetophenone (4 g, 21.15 mmol, Aldrich) in dry MeOH (80 mL), sodium borohydride (0.96 g, 25.39 mmol, spectrochem) was added portionwise at 0 C. The reaction mixture was stirred at rt overnight. It was cooled to 0 C and quenched using ice water (10 mL). Solvents were removed under reduced pressure and resulting residue was dissolved in DCM (50 mL). The organic layer was washed with water (25 mL), brine (20 mL), dried over Na2SO4 and concentrated. The crude product was used for next step without further purification. Yield: 95% (3.8 g, colorless liquid). 1H NMR (400 MHz, DMSO-d6): delta 7.57-7.55 (m, 2H), 7.33 (d, J = 1.9 Hz, 1H), 5.38 (d, J = 4.4 Hz, 1H), 4.76-4.70 (m, 1H), 1.30 (d, J = 6.4 Hz, 3H).
	With methanol; sodium tetrahydroborate; at 0 - 20℃;	General procedure: Ten mmol of NaBH4 was added to a cooled (0C) solution of 2.5 mmol of each specific substrate(1a-1f, 1m and 1n) in 50 mL of methanol. After stirring for 10 min, the mixture was warmed to room temperature and stirred for another 3-4 h to complete the reduction. After quenching with 2 M HCl topH 7.0, the mixture was extracted with EtOAc (50 mL 3). The organic phases were washed withbrine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by flashchromatography on silica gel (eluent: EtOAc/PE 1:20) to give the racemic alcohol 2a-2f, 2m and 2n(see Supplementary Materials for NMR spectroscopic data).

References: [1]Synthesis,2009,p. 4058 - 4062.
[2]Patent: CN109384645,2019,A .Location in patent: Paragraph 0060; 0061; 0062; 0063.
[3]Tetrahedron,2019,vol. 75.
[4]Journal of Medicinal Chemistry,1997,vol. 40,p. 3905 - 3914.
[5]Molecular catalysis,2018,vol. 448,p. 153 - 161.
[6]Tetrahedron Letters,2020,vol. 61.
[7]Patent: WO2016/30443,2016,A1 .Location in patent: Page/Page column 93.
[8]Marine Drugs,2018,vol. 16.

6
[ 52909-94-1 ]
[ 60-29-7 ]
lithium borate [ No CAS ]
[ 1475-11-2 ]
[ 35364-79-5 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 5612.

7
[ 52909-94-1 ]
[ 64-17-5 ]
platinum [ No CAS ]
[ 1475-11-2 ]
[ 35364-79-5 ]

References: [1]Journal of Organic Chemistry,1957,vol. 22,p. 93.

9
(+-)-<3,4-dichloro-phenyl>-oxirane [ No CAS ]
[ 1475-11-2 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 5612.

10
[ 1475-11-2 ]
[ 545-06-2 ]
[ 820260-69-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

11
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-amino-3-[1-(3,4-dichlorophenyl)ethoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

12
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-amino-3-[1-(3,4-dichlorophenyl)ethoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

13
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

14
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

15
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

16
[ 1475-11-2 ]
(1S,2R,3R,5R,6S)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3405 - 3420.

17
[ 1475-11-2 ]
(1R,2R,3R,5R,6R)-2-amino-3-(1-(3,4-dichlorophenyl)ethoxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

18
[ 1475-11-2 ]
(1R,2R,3R,5R,6R)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

19
[ 1475-11-2 ]
(1R,2R,3R,5R,6R)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

20
[ 1475-11-2 ]
[ 52909-94-1 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3905 - 3914.

21
[ 1475-11-2 ]
1-(3,4-Dichloro-phenyl)-2-((1R,3S,5S)-3-phenyl-8-aza-bicyclo[3.2.1]oct-8-yl)-ethanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3905 - 3914.

22
[ 95-50-1 ]
[ 1475-11-2 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1105,1107.

23
[ 110-89-4 ]
[ 1475-11-2 ]
[ 459451-08-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 169 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(3,4-dichlorophenyl)-ethyl Ester The procedure for Example 65 was followed, substituting (3,4-dichlorophenyl)-ethan-1-ol for (S)-phenylethanol, and substituting piperidine for diethylamine. ESI+MS m/z 459 (M+1).

References: [1]Patent: US2003/64991,2003,A1 .

24
[ 1897-52-5 ]
[ 1475-11-2 ]
[ 872181-29-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 78; 5-[1-(3,4-Dichlorophenyl)-ethoxy]-quinazoline-2,4-diamine; [00244] Step 1; To a cold (ice water) suspension of sodium hydride (316 mg; 7.9 mmol) in anhydrous DMF (10 mL) is added a solution of 1-(3,4-dichlorophenyl)- ethanol (1.40 g; 7.3 mmol) in anhydrous DMF (5 mL) over 30 minutes. After allowing to room temperature over 30 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1.0 g; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature over 2 hours. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed and the resulting oil is dried under vacuum at 30 C overnight to give 1.93 gm of 2-[1- (3,4-dichlorophenyl) -ethoxy]-6-fluorobenzonitrile.

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 449 - 469.
[2]Patent: WO2005/123724,2005,A1 .Location in patent: Page/Page column 58.

25
[ 1475-11-2 ]
4-(1-bromoethyl)-1,2-dichlorobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; phosphorus tribromide; In n-heptane; at 0 - 20℃; for 2h;	To a solution of <strong>[1475-11-2]1-(3,4-dichlorophenyl)ethanol</strong> (0.87 g, 4.55 mmol)in n-heptane (5.00 mL) and Et2O (0.500 mL) at 0 C. was added pyridine (1 drop) and phosphorous tribromide (0.214 mL, 2.277 mmol). The reaction mixture was warmed to RT and stirred for 2 h. The reaction was diluted with ether, washed with water (1), saturated NaHCO3 (1), and brine (1*). The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 4-(1-bromoethyl)-1,2-dichlorobenzene (0.985 g, 3.88 mmol, 85% yield). m/z (ESI) 249.0 (M+H)+.
77%	With phosphorus tribromide; In dichloromethane; at 20℃;	1-(3,4-Dichlorophenyl)ethan-1-ol (500 mg, 2.64 mmol) and 37 phosphorus tribromide (850 mg, 3.14 mmol) were dissolved in 29 dichloromethane (20 mL). The reaction mixture was stirred for overnight at room temperature. The reaction mixture was quenched with 38 ice water. The reaction was washed with saturated sodium bicarbonate followed by brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0 to 30% ethyl acetate/hexane) to give the 33 product as a white solid (508 mg, 77%); 1H NMR (300 MHz) (CDCl3) delta7.53 (s, 1H), 7.43-7.40 (d, 1H), 7.29-7.26 (d, 1H), 5.12-5.07 (q, 1H), 2.03-2.00 (s, 3H).

References: [1]Patent: US9212182,2015,B2 .Location in patent: Page/Page column 222; 223.
[2]Patent: US2019/31624,2019,A1 .Location in patent: Paragraph 0412-0413.

26
[ 1475-11-2 ]
[ 107-21-1 ]
2-bromomethyl-2-(3,4-dichlorophenyl)-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 20℃; for 24h;	General procedure: A mixture of 2 mmol of substrate, and 4 mL ethylene glycol was stirred for 5 min, and then 2.4 mmol of DBDMH or 4.6 mmol of NBS was added by 5 times in one hour, and the mixture was stirred 24 h at room temperature. Afterward, the mixture was extracted with ether (10 mL × 3). The combined organic layer was washed twice by water (20 mL), and dried over anhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure, and the residual was treated with alumina chromatography (Petroleum ether/AcOEt=20/1,V/V) to generate the product.

References: [1]Synthetic Communications,2017,vol. 47,p. 2387 - 2394.

27
[ 75-16-1 ]
[ 6287-38-3 ]
[ 1475-11-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 0 - 20℃; for 3.16667h;Inert atmosphere;	General procedure: To a solution of aldehyde 11 (4mmol) in THF (12mL) at 0C under nitrogen, was dropwise added methylmagnesium bromide (1.0M in THF, 5mmol). After stirring for 10min the reaction mixture was allowed to warm to room temperature and was stirred for 3h. Upon completion, the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude residue was used directly.