10599-69-6|1-(5-Methylfuran-2-yl)propan-1-one| Ambeed

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Quality Control of [ 10599-69-6 ] Purity: 97% SDS Specification

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Product Details of [ 10599-69-6 ]

CAS No. :	10599-69-6
Formula :	C₈H₁₀O₂
M.W :	138.16
SMILES Code :	CCC(=O)C1=CC=C(C)O1
MDL No. :	MFCD00053142
InChI Key :	BXLPZYAVKVFXEO-UHFFFAOYSA-N
Pubchem ID :	82757

Safety of [ 10599-69-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P302+P352-P305+P351+P338

Application In Synthesis of [ 10599-69-6 ]

* 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 [ 10599-69-6 ]
Downstream synthetic route of [ 10599-69-6 ]

[ 10599-69-6 ] Synthesis Path-Upstream 1~1

1
[ 10599-69-6 ]
[ 2364-75-2 ]

References: [1] Canadian Journal of Chemistry, 1953, vol. 31, p. 564,566.
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 1, p. 181 - 183.

[ 10599-69-6 ] Synthesis Path-Downstream 1~35

1
[ 1117-96-0 ]
[ 620-02-0 ]
[ 10599-69-6 ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 2737.

2
[ 534-22-5 ]
[ 123-62-6 ]
[ 10599-69-6 ]

Yield	Reaction Conditions	Operation in experiment
95.3%	With phosphoric acid; In dichloromethane; water; at 120℃; for 1h;	1) Put 32g of propionic anhydride into a 250mL three-necked flask, add 0.3g phosphoric acid and 0.3g polyphosphoric acid dropwise to 120C, add 16.4g 2-methylfuran dropwise, continue the reaction at 120C for 0.5 hours, add water after cooling down 100g and 100g of dichloromethane were stirred for 0.5 hours and then left to stand for liquid separation. Dichloromethane was distilled out under normal pressure and then distilled under reduced pressure to obtain 26.3g of 2-propionyl-5-methylfuran. The purity by GC was 99.0%. The rate is 95.3%.

References: [1]Patent: CN112724076,2021,A .Location in patent: Paragraph 0020; 0021; 0023; 0024; 0026; 0027.
[2]Liebigs Annalen der Chemie,1985,p. 1935 - 1950.
[3]Journal of Organic Chemistry,1984,vol. 49,p. 4523 - 4531.
[4]Canadian Journal of Chemistry,1953,vol. 31,p. 564,566.
[5]Bulletin de la Societe Chimique de France,1957,p. 1311,1315.
[6]Journal of the American Chemical Society,1950,vol. 72,p. 3695,3696, 3697.
[7]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 181 - 183.

3
[ 10599-69-6 ]
[ 107-15-3 ]
[ 138350-45-5 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 597 - 600.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 763 - 766.

4
[ 10599-69-6 ]
[ 10424-38-1 ]
1-Ethyl-3,6-dimethyl-3,4-dihydro-pyrrolo[1,2-a]pyrazine [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 766 - 771.
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 921 - 928.

5
[ 62968-77-8 ]
[ 10599-69-6 ]
[ 72185-13-8 ]
[ 62968-84-7 ]
[ 62968-85-8 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 4523 - 4531.

Yield	Reaction Conditions	Operation in experiment
41.5%		After completion of the reaction, post-treatment was carried out in the same manner as in Example 3 to obtain 2.87 g of 2-propionyl-5-methylfuran. Yield: 41.5% nD25: 1.5087

8
[ 10599-69-6 ]
1-Ethyl-3,6-dimethyl-pyrrolo[1,2-a]pyrazine [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 766 - 771.
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 921 - 928.

9
[ 10599-69-6 ]
[ 138350-50-2 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 597 - 600.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 763 - 766.

10
[ 10599-69-6 ]
N-(3,7-Dimethyl-indolizin-8-yl)-N-methyl-acetamide [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 597 - 600.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 763 - 766.

11
[ 10599-69-6 ]
[ 138350-40-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 597 - 600.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 763 - 766.

12
[ 10599-69-6 ]
[ 138350-48-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 597 - 600.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 763 - 766.

13
[ 10599-69-6 ]
[ 64271-00-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 181 - 183.

14
[ 98-01-1 ]
[ 10599-69-6 ]

References: [1]Bulletin de la Societe Chimique de France,1957,p. 1311,1315.

15
[ 10599-69-6 ]
[ 75-29-6 ]
[ 1000993-74-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		Under nitrogen, <strong>[10599-69-6]2-methyl-5-propionylfuran</strong>e (100 g, 0.72 moles) was added dropwise at 0-300C to aluminium chloride (131 g, 0.96 moles). The resulting suspension was stirred for further 30 minutes at room temperature and then cooled to 0-50C. Within one hour isopropyl chloride (76 g, 0.96 moles) was added dropwise at 0-10C and the mixture stirred until complete conversion was achieved (HPLC). The mixture was hydrolyzed on 2 L of water/ice. The pH was adjusted to 1 by addition of sodium hydroxide solution (60 mL) and the product was extracted into 500 mL TBME. The aqueous layer was separated and reextracted with 200 mL TBME. The combined organic layers were washed with 500 mL brine and evaporated to minimum volume. Yield: 132.5 g (102%) of a yellow-brown liquid.Assay (HPLC: YMC Pack Pro C18 150x4.6 mm, 5 μm; 220 nm; ACN/0.05% TFA : water/0.05% TFA 20:80 to 95:5 within 23 min): 60% pure by area, RT 17.2 min.
100%		Under nitrogen, <strong>[10599-69-6]2-methyl-5-propionylfuran</strong>e (120 g, 0.87 moles) was added dropwise at 0-350C to aluminium chloride (158 g, 1.18 moles) in dichloromethane (60 ml). The resulting solution was stirred for further 30 minutes at room temperature and then cooled to 0-5C. Within one hour isopropyl chloride (96 g, 1.21 moles) was added dropwise at 0-10C and the mixture was stirred at 0-5C until complete conversion was achieved. The mixture was hydrolyzed on 2 L of water/ice and TBME (480 mL ) was added. The pH was adjusted to 1 by addition of sodium hydroxide solution 30% (50 mL) and the phases were split. The aqueous layer was reextracted into 240 mL TBME. The combined organic layers were washed with 300 mL brine twice and evaporated to minimum volume. Yield: 168 g (107%) of a yellow- brown liquid.
		Step 1: 1-(4-lsopropyl-5-methyl-2-furyl)propan-1-one (206). Under nitrogen, <strong>[10599-69-6]2-methyl-5-propionylfuran</strong>e (100 g, 0.72 moles) was added dropwise at 0-300C to aluminium chloride (131 g, 0.96 moles). The resulting suspension was stirred for further 30 minutes at room temperature and then cooled to 0-50C. Within one hour isopropyl chloride (76 g, 0.96 moles) was added dropwise at 0-10C and the mixture stirred until complete conversion was achieved (HPLC). The mixture was hydrolyzed on 2 L of water/ice. The pH was adjusted to 1 by addition of sodium hydroxide solution (60 mL) and the product was extracted into 500 mL TBME. The aqueous layer was separated and reextracted with 200 mL TBME. The combined organic layers were washed with 500 mL brine and evaporated to minimum volume. Yield: 132.5 g (102%) of a yellow-brown liquid. Assay (HPLC: YMC Pack Pro C18 150x4.6 mm, 5 μm; 220 nm; ACN/0.05% TFA : water/0.05% TFA 20:80 to 95:5 within 23 min): 60% pure by area, RT 17.2 min.

References: [1]Patent: WO2009/5801,2009,A1 .Location in patent: Page/Page column 40-41.
[2]Patent: WO2009/5801,2009,A1 .Location in patent: Page/Page column 40; 43.
[3]Patent: WO2009/5802,2009,A1 .Location in patent: Page/Page column 27.

16
[ 10599-69-6 ]
[ 60100-09-6 ]
[ 1099823-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; at 20 - 150℃; for 14 - 18h;Product distribution / selectivity;	To a stirred solution of 100 g <strong>[10599-69-6]2-methyl-5-propionylfuran</strong> (1.0 equiv., 0.724 mol) and 115 mL formamide (2.90 mol, 4.0 equiv.) at 25 0C was added 30.0 mL formic acid (0.796 mol, 1.1 equiv.). A small exotherm was observed. The resulting solution was heated to 140-150 0C over 1 hour, held at this temperature for 12 hours, and then cooled to 20-30 0C over 1 hour. To the stirred solution of crude intermediate amide product was added 641 mL 25% w/w aq. NaOH (5.07 mol NaOH, 7.0 equiv.). An exotherm was observed. The heterogeneous solution was vigorously agitated to achieve a homogeneous mixture. The solution was heated to 65-70 0C over 30 min., held at this temperature for 10 hours, then cooled to 20-30 0C over 1 hour. The phases were allowed to separate, drained the aqueous layer, then washed the <n="39"/>organic layer of crude racemic amine twice with 10% aq. NaCI (100 ml_). The crude racemic amine was taken up in 350 mL methanol and 28 mL water. The solution was heated to 50-60 0C and to it was added 73.5 g D-tartaric acid (0.502 mol, 1.0 equiv.) as a solution in 210 mL methanol and 14 mL water over 30 minutes. The reaction was held at 60 0C for 15 min, then cooled to 15-35 0C over 2 hours. The suspension was then filtered under vacuum and washed twice with 70 mL methanol. The wet cake was dried in a vacuum oven at 50-60 0C for at least 8 hours to afford 60.1 g (28.7% yield, 99% ee) of a white crystalline solid; mp = 191-1940C; 1H NMR (DMSO-D6): δ 0.81 (t, 3H, J=7.4 Hz), 1.79-1.95 (m, 2H), 2.26 (s, 3H), 3.99 (s, 2H), 4.18 (dd, 1H, J=8.9, 5.7 Hz)1 6.07 (dd, 1H, J=3.1, 1.1 Hz), 6.38 (d, 1H, J=3.1 Hz), and 8.16 (brs, 6H). 13C NMR (DMSO-D6): 10.31, 13.63, 25.46, 49.40, 72.31, 107.03, 109.98, 149.46, 152.01, 175.01 ppm.EXAMPLE IVa Alternative Preparation of tartarate salt of α-(R)-Ethyl-5-methyl-2-furanmethanamine D-tartrate (2DaD2-methy1-5-propionyl furan Intermediate AmideTo a stirred solution of 60 g <strong>[10599-69-6]2-methyl-5-propionylfuran</strong> (1.0 equiv., 0.434 mol) and 69 mL formamide (1.74 mol, 4.0 equiv.) at 25 0C was added 16.4 mL formic acid (0.434 mol, 1.0 equiv.). The resulting solution was heated to 140-150 0C over 1 hour, held at this temperature for 16 hours, and then cooled to 20-30 0C over 1 hour. To the stirred solution of crude intermediate amide product was added 377 mL 25% w/w aq. NaOH (2.89 mol NaOH1 7.0 <n="40"/>equiv.). The heterogeneous solution was vigorously agitated to achieve a homogeneous mixture. The solution was heated to 80-90 0C over 30 min., held at this temperature for 6 hours, then cooled to 20-30 0C over 1 hour. The phases were allowed to separate, and the aqueous layer was drained. The crude racemic amine was distilled under vacuum (20-25 mmHg) to afford 50.1 g (82% yield) of a pale yellow oil; bp = 60-65 0C (40-45 mmHg); 1H NMR (DMSO-D6): δ 0.84 (3H, t, J = 7.4 Hz), 1.49-1.58 (1H, m), 1.61-1.71 (1H, m), 1.61 (2H, brs), 2.21 (3H, s), 3.63 (1H, t, J = 6.54 Hz), 5.93 (1H, dd, J = 2.98, 1.00 Hz), 6.00 (1H, d, J = 1.0 Hz); 13C NMR (DMSO-D6): 10.6, 13.6, 29.7, 51.1, 105.2, 106.1, 149.8, 158.5 ppm. To a solution of the racemic amine in 250 mL methanol was added 50.5 g D-tartaric acid (336.5 mmole) as a solution in 150 mL methanol over 30 minutes. The solution was heated to 40- 50 0C and held at this temperature for 20 minutes. The reaction was slowly cooled to 0-10 0C over 2 hours. The suspension was then filtered under vacuum and washed with methanol (100 mL). The wet cake was dried in a vacuum oven at 50-60 0C for at least 8 hours to afford 44.1 g (42.3% yield from racemic amine, 94% ee) of a white crystalline solid; characterized as above.

References: [1]Patent: WO2009/5801,2009,A1 .Location in patent: Page/Page column 37-39.

17
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[ 6952-59-6 ]
[ 1160844-01-8 ]