2790-74-1|Methyl 1-methoxycyclopropanecarboxylate| Ambeed

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CAS No. :	2790-74-1
Formula :	C₆H₁₀O₃
M.W :	130.14
SMILES Code :	O=C(C1(OC)CC1)OC
MDL No. :	MFCD20483714

Yield	Reaction Conditions	Operation in experiment
98%		Example B6 A 0 C. solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropane-1-carboxylate</strong> (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3*). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).
98%		Example B18 A 0 C. solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropane-1-carboxylate</strong> (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3×). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).
	With sodium hydride; In tetrahydrofuran; at 0℃; for 18h;	Step A: 1-METHOXV-CVCLOPROPANECARBOXYLIC acid methyl ester 1-Hydroxy-cyclopropanecarboxylic acid methyl ester (1.16 gm, 10 MMOL) was dissolved in 10 ml of tetrahydrofuran and cooled under a nitrogen atmosphere to 0 C. Sodium hydride (0.52 gm, 60 % oil dispersion) was added portionwise followed by lodomethane (1 ml) and stirred for 18 hrs. The reaction mixture was quenched with ammonium chloride and extracted with ETHYLACETATE to obtain 2 gm of title product. (MH+= 130)

	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 18h;	According to WO 2005/014577 methyl l-hydroxycyclopropanecarboxylate (1.01 g, 8.70 mmol) was dissolved under argon in THF (10 ml) and cooled using an ice-bath. Sodium hydride (60%, 0.52 g, 13.00 mmol) was added portionwise followed by iodomethane (1 ml, 16.06 mmol) and the mixture was stirred for 18 hours at room temperature. The mixture was quenched with saturated solution OfNH4Cl (20ml) and extracted with EtOAc. The organic extracts were combined, dried, filtered and evaporated in vacuo to give 620 mg of the crude product which was used as such.1H NMR (400 MHz, CDCl3) delta 3.76 (s, 3H), 3.43 (s, 3H), 1.25-1.17 (b, 4H),
4.0 g		To a solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (3.2 g) in tetrahydrofuran (40 ml), sodium hydride (55% oil, 1.3 g) was added under ice cooling, and the mixture was stirred at the same temperature as above for 15 minutes. Methyl iodide (2.3 ml) was added to the reaction solution, and the mixture was stirred overnight at room temperature. 1 N hydrochloric acid was added to the reaction solution, followed by extraction with a n-hexane-ethyl acetate mixed solution. The extract was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (4.0 g). 1H-NMR (CDCl3) delta: 1.13-1.32 (4H, m), 3, 42 (3H, s), 3.75 (3H, s).
		00512] Step A: NaH (738 mg, 18.44 mmol; 60% dispersion in oil) was added to a solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (1.83 g, 14.18 mmol) in anhydrous THF (15 mL) cooled on an ice bath. The mixture was stirred for 15 minutes then iodomethane (3.22 g, 1.42 mL, 22.69 mmol) was added slowly, and the resulting mixture stirred at ambient temperature for 18 hours. The reaction mixture was quenched with ammonium chloride and extracted with EtOAc (3 X 20 mL). The combined organic extracts were washed with water, <n="167"/>dried over MgSO4, and filtered. The filtrate was evaporated under reduced pressure to give methyl 1-methoxycyclopropanecarboxylate.

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CAS No.: 2790-74-1

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CAS No.: 2790-74-1

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[ 2790-74-1 ] Synthesis Path-Downstream 1~1

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H201	Explosive; mass explosion hazard
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H220	Extremely flammable gas
H221	Flammable gas
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H226	Flammable liquid and vapour
H227	Combustible liquid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H250	Catches fire spontaneously if exposed to air
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