38806-09-6|Methyl 1-acetylcyclopropanecarboxylate| Ambeed

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Quality Control of [ 38806-09-6 ] Purity: 97% SDS Specification

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Product Details of [ 38806-09-6 ]

CAS No. :	38806-09-6
Formula :	C₇H₁₀O₃
M.W :	142.15
SMILES Code :	O=C(C1(C(C)=O)CC1)OC
MDL No. :	MFCD11226171
InChI Key :	JXBAKCMWFYJKGF-UHFFFAOYSA-N
Pubchem ID :	10214400

Safety of [ 38806-09-6 ]

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

Application In Synthesis of [ 38806-09-6 ]

* 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.

Downstream synthetic route of [ 38806-09-6 ]

[ 38806-09-6 ] Synthesis Path-Downstream 1~35

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[ 38806-09-6 ]

References: [1]Bulletin of the Chemical Society of Japan,1972,vol. 45,p. 1884 - 1888.

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[ 357914-49-9 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 436 - 441.

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References: [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 146 - 153.

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[ 73959-42-9 ]

References: [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 146 - 153.

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[ 38806-09-6 ]
[ 141-43-5 ]
[ 116195-43-8 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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[ 107-21-1 ]
[ 124572-91-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium p-toluenesulfonate; In toluene; for 20h;Reflux; Dean-Stark;	Methyl 1-acetylcyclopropanecarboxylate (5.02 g,35.3 mmol, 1 equiv) and pyridinium-paratoluenesulfonate (1.36 g,5.30mmol, 0.15 equiv) were dissolved in 150 ml of toluene. Ethylene glycol (7.80 ml, 141 mmol, 4.00 equiv) was added and the reaction was stirred at reflux with a Dean-Starck apparatus for 20 h until no more water was formed. Toluene and ethylene glycol were removed by distillation. The reaction was concentrated then dissolved with 45 ml of ethanol. 2 M NaOH aqueous solution (45.0 ml, 90.0 mmol, 2.50 equiv) was added and the reactionwas stirred at 25 C for 19 h to give a yellow suspension. The reaction was saturated with NaCl and acidified with 6 N HCl to reach a persistent pH 4. The mixture was extracted with 350 ml of DCM. Combined organic layers were dried over MgSO4, and concentrated. The crude was purified by flash chromatography over silica gel, petroleum ether/EtOAc (95/5 to 20/80) to give 4.35 g of a white solid (71%). 1H NMR (300MHz, CDCl3) dH1.03e1.06 (2H, m, CH2eCH2), 1.21e1.26 (2H, m, CH2eCH2), 1.57 (3H,s, CH3eCOO), 3.93e4.04 (4H, m, OeCH2eCH2eO). 13C NMR(75.47 MHz, CDCl3) dC 13.6 (CH2, CH2eCH2), 24.1 (CH3, CeCH3), 30.4(C, COOeCeCOOH), 65.3 (CH2, OeCH2eCH2eO),108.1 (C, COO),178.1(C, COOH). IR (KBr) n: 3431 (br.), 1689, 1050 cm1. m/z HR-MS: (DCI/CH4): calculated for C8H13O4 173.0814, found 173.0818.

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2741 - 2744.
[2]Journal of the Chemical Society. Chemical communications,1989,p. 690 - 691.
[3]Tetrahedron,2013,vol. 69,p. 6709 - 6720.

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Yield	Reaction Conditions	Operation in experiment
67%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 96h;	1-Acetylcyclopropanecarboxylic acid methyl ester (28)To a vigorously stirred suspension of anhydrous K2 CO3 (40.0 g; 290 mmol) in acetonitrile (100 ml), tetra-n-butylammonium bromide (3.20 g; 10.0 mmol), 1,2-dibromoethane (13.0 ml; 28.4 g; 150 mmol) and methyl acetoacetate 27 (10.8 ml; 11.6 g; 100 mmol) were added. The reaction mixture was stirred for 4 days. The solids were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by distillation under reduced pressure to give 9.55 g (67.0 mmol; 67% yield) of 28. 1H NMR (400 MHz, CDCl3) δ 1.48 (4H, s), 2.47 (3H, s), 3.75 (3H, s); 13C NMR (101 MHz, CDCl3) δ 19.3, 29.8, 34.9, 171.5, 203.0; MS (EI) m/z 143 ([M+H]+, 100), 142 (M+, 70), 127 (81), 111 (87); exact mass calculated for C7H11O3 ([M+H]+) 143.0708. found 143.0705.
67%		K2CO3 (11.9 g, 86.0 mmol, 2.50 equiv) was suspended in 35 ml of acetone. Methylacetoacetate (3.70 ml, 34.4 mmol, 1.00 equiv) was added dropwise to the suspension. The mixture was stirred at room temperature for 20 min. 1,2-Dibromoethane (6.00 ml, 68.9 mmol, 2.00 equiv) was added and the reaction was stirred at reflux for 26 h. The reaction was filtered and concentrated. The crude mixture was purified by flash chromatography, using petroleum ether/EtOAc (95/5 to 90/10) to give 3.26 g (67% yield) of a colorless oil. Rf (petroleum ether/EtOAc:90/10) 0.50. 1H NMR (300 MHz, CDCl3) dH 1.47 (4H, s,CH2eCH2), 2.46 (3H, s, COeCH3), 3.74 (3H, s, COOCH3).
52%	With potassium carbonate; In acetone; for 36h;Reflux;	To a mixture of methyl 3-oxobutanoate (10 g, 86 mmol), potassium carbonate (29.8 g, 36 mmol) and acetone (150 mL) was added 1,2-dibromoethane (21 g, 112 mmol) and the mixture was heated under reflux for 1.5 days. The reaction mixture was cooled to room temperature, insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (97:3-3:1)] to give the title compound (6.41 g) as a colorless oil (yield 52%). 1H NMR (300 MHz, CDCl3) δ 1.48 (4H, s), 2.47 (3H,s), 3.75 (3H,s).

37%	With potassium hydroxide; In hexane; dimethyl sulfoxide;	a) Methyl 1-Acetylcyclopropylcarboxylate Methyl acetoacetate (8.6ml, 80mmol), 1,2-dibromoethane (7ml, 80mmol) and potassium hydroxide (11.2g, 200mmol) in DMSO (80ml) were stirred for 48h, poured into water, acidified and extracted with ether (3x50ml). The extracts were washed with water (2x100ml) and brine 50ml), dried, concentrated and flash chromatographed on silica gel eluding with 5-10% ethyl acetate in hexane to yield the title compound (4.18g, 37%); δH(90MHz, CDCl3) 1.46 (4H,s), 2.44 (3H,s), 3.72 (3H,s).
	With potassium carbonate; In acetone; at 20℃; for 8h;Heating / reflux;	Reference Example 87 To a mixture of methyl acetoacetate (10.0 g), potassium carbonate (29.8 g), and acetone (145 mL) was added 1,2-dibromoethane (21.0 g) at room temperature, and the mixture was heated under reflux for 8 hours. The reactant was concentrated after cooling to room temperature. The obtained residue was purified by silica gel column chromatography to obtain methyl 1-acetylcyclopropanecarboxylate (1.90 g). 1H-NMR (300 MHz, CDCl3) δ: 1.49 (4H, s), 2.47 (3H, s), 3.75 (3H, s).
2.17 g	With potassium carbonate; In acetone; at 65℃; for 17h;	To a solution of methyl acetoacetate (3 ml) in acetone (30 ml) were sequentially added potassium carbonate (11.54 g) and 1,2-dibromoethane (2.4 ml) at room temperature, and the mixture was stirred at 65 C. for 17 hours. This reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1) to give the titled compound (2.17 g). 1H-NMR (CDCl3) δ: 1.48 (s, 4H), 2.47 (s, 3H), 3.75 (s, 3H).
0.7 mol	With potassium carbonate; In acetone; at 70℃; for 24h;	Step a. To a solution of methyl acetoacetate (1.72 mol) and 1,2-dibromoethane (1.90 mol) in acetone (2000 ml) was added K2CO3 (2.59 mol) at rt. The reaction mixture was heated at 70C for 24 h. The resulting reaction mixture was allowed to cool to rt and filtered through celite hyflow. The celite cake was washed with acetone (2 x 100 ml). The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography (4% EtOAc in hexane) yielding methyl 1-acetylcyclopropane-l-carboxylate (0.70 mol). MS: ES+ 143.14.
100 g	With potassium carbonate; In acetone; at 70℃; for 24h;	To a solution of methyl acetoacetate (200 g, 1724.13 mmol) and 1 ,2- dibromoethane (179.2 mL, 2068.95 mmol) in acetone (2000 mL) was added K2CO3 (356.8 g, 2586.19 mmol) at rt. The reaction mixture was heated at 70C for 24 h. The resulting mixture was cooled to rt, filtered through celite and washed with acetone (2 x 100 mL). The filtrate was concentrated under reduced pressure to give a crude oil which was purified by column chromatography (4% EtOAc in hexane) to yield methyl 1 -acetylcyclopropane-1 -carboxylate (100 g, 704.22 mmol). LCMS: Method C, 1 .47 min, MS: ES+ 143.14
100 g	With potassium carbonate; In acetone; at 70℃; for 24h;	To a solution of methyl acetoacetate (200 g, 1724.13 mmol) and 1,2-dibromoethane (179.2 mL, 2068.95 mmol) in acetone (2000 mL) was added K2C03 (356.8 g, 2586.19 mmol) at rt. The reaction mixture was heated at 70C for 24 h. The resulting mixture was cooled to rt, fdtered through celite and washed with acetone (2 x 100 mL). The filtrate was concentrated under reduced pressure to give a crude oil which was purified by column chromatography (4% EtOAc in hexane) to yield methyl 1-acetylcyclopropane-l-carboxylate (100 g, 704.22 mmol). LCMS: Method C, 1.47 min, MS: ES+ 143.14.

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2741 - 2744.
[2]Journal of Organic Chemistry,1992,vol. 57,p. 436 - 441.
[3]Patent: US2012/309719,2012,A1 .Location in patent: Page/Page column 19.
[4]Tetrahedron,2013,vol. 69,p. 6709 - 6720.
[5]Journal of the American Chemical Society,2008,vol. 130,p. 875 - 886.
[6]Patent: EP2530078,2012,A1 .Location in patent: Page/Page column 159.
[7]Patent: EP354757,1991,A3 .
[8]Patent: EP1553074,2005,A1 .Location in patent: Page/Page column 52.
[9]Patent: US2013/85132,2013,A1 .Location in patent: Paragraph 1050; 1051; 1052.
[10]Patent: WO2016/46530,2016,A1 .Location in patent: Page/Page column 59.
[11]Patent: WO2018/234775,2018,A1 .Location in patent: Page/Page column 38.
[12]Patent: WO2019/171042,2019,A1 .Location in patent: Page/Page column 35.
[13]Chemistry - A European Journal,2020.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.

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References: [1]Tetrahedron Letters,1987,vol. 28,p. 6597 - 6600.
[2]Chemistry - A European Journal,2020.

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(E)-3-(2-Bromo-ethoxy)-but-2-enoic acid methyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 525 - 530.

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References: [1]Synthetic Communications,1996,vol. 26,p. 525 - 530.

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References: [1]Synthetic Communications,1996,vol. 26,p. 525 - 530.

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Yield	Reaction Conditions	Operation in experiment
	In toluene; for 12h;Heating / reflux;	Reference Example 88 A mixture of <strong>[38806-09-6]methyl 1-acetylcyclopropanecarboxylate</strong> (1.40 g), [(1S)-1-phenylethyl]amine (1.26 mL), and toluene (18 mL) was heated under reflux for 12 hours. The reactant was concentrated after cooling to room temperature. The obtained residue was purified by silica gel column chromatography to obtain methyl 2-methyl-1-[(1S)-1-phenylethyl]-4,5-dihydro-1H-pyrrole-3-carboxylate (1.29 g). 1H-NMR (300 MHz, CDCl3) δ: 1.54 (3H, d, J=7.2 Hz), 2.33 (3H, s), 2.64-2.72 (2H, m), 3.10-3.20 (1H, m), 3.37-3.48 (1H, m), 3.63 (3H, s), 4.88 (1H, q, J=7.2 Hz), 7.21-7.38 (5H, m).
0.37 mol	In toluene; at 130 - 140℃; for 22h;Dean-Stark;	Step b. A solution of methyl 1-acetylcyclopropane-l-carboxylate (0.70 mol) and (S)-l- phenylethan-1 -amine (0.84 mol) in toluene (1000 ml) was charged in a dean stark glass assembly. The reaction mixture was heated at a temperature (130-140C) to remove the water by azeotropic distillation. The process was continued for 22 h. The reaction mixture was allowed to cool to rt and concentrated under reduced pressure. The resulting residue was purified by column chromatography (2% EtOAc in hexane) yielding methyl (S)-2-methyl-l- (l-phenylethyl)-4,5-dihydro-lH-pyrrole-3-carboxylate (0.37 mol). MS: ES+ 246.33; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.36 - 7.39 (m, 2 H), 7.26 - 7.29 (m, 3 H), 4.95 (q, J=7.01 Hz, 1 H), 3.50 (s, 3 H), 3.41 - 3.49 (m, 1 H), 3.03 - 3.10 (m, 1 H), 2.55 - 2.57 (m, 2 H), 2.25 (s, 3 H), 1.48 (d, J=7.01 Hz, 3 H).

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 3122 - 3131.
[2]Journal of the American Chemical Society,2008,vol. 130,p. 875 - 886.
[3]Patent: EP1553074,2005,A1 .Location in patent: Page/Page column 52.
[4]Patent: WO2016/46530,2016,A1 .Location in patent: Page/Page column 59.

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