1-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester → 1-[(Methylsulfanyl)methyl]cyclopropane-1-carboxylic acid

Temperature

23 °C

Preparation of ethyl 1-(methylthiomethyl)cyclopropanecarboxylate—Sodium methanethiolate (700 mg, 9.9 mmol, 2.0 equiv) was added to a stirred solution of ethyl 1-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (1.1 g, 4.9 mmol, 1.0 equiv) in N,N-dimethylformamide (10 mL) at 23° C. The resulting brown suspension was stirred at 23° C. for 18 h. The reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (4×100 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a brown oil (860 mg, 99%): 1H NMR (300 MHz, CDCl3) δ 4.14 (q, J=7 Hz, 2H), 2.83 (s, 2H), 2.16 (s, 3H), 1.31 (dd, J=7, 4 Hz, 2H), 1.25 (t, J=7 Hz, 3H), 0.89 (dd, J=7, 4 Hz, 2H).

1. extractionextracted with diethyl ether (4×100 mL)
2. dry with materialThe combined organic layers were dried (MgSO4)
3. filtrationgravity-filtered
4. concentrationconcentrated by rotary evaporation

ORD record

ord-1b4474e2263d4383a675a36f849f4c44

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604211B2