Methanesulfonyl chloride → 1-[(Methylsulfanyl)methyl]cyclopropane-1-carboxylic acid
Reaction equation
CS(O[CH2:6][C:7]1([C:10]([O:12]CC)=[O:11])[CH2:9][CH2:8]1)(=O)=O.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=O)=O.OCC1(C(OCC)=O)CC1>ClCCl.O>[CH3:22][S:23][CH2:6][C:7]1([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
Preparation of ethyl 1-((methylsulfonyloxy)methyl)cyclopropanecarboxylate—Triethylamine (990 μL, 7.1 mmol, 1.2 equiv) and methanesulfonyl chloride (500 μL, 6.5 mmol, 1.1 equiv) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (840 mg, 5.7 mmol, 1.0 equiv) in dichloromethane (15 mL) at 23° C. The resulting bright yellow solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a brown oil (1.1 g, 85%): 1H NMR (300 MHz, CDCl3) δ 4.33 (s, 2H), 4.16 (q, J=7 Hz, 2H), 3.08 (s, 3H), 1.43 (dd, J=7, 4 Hz, 2H), 1.26 (t, J=7 Hz, 3H), 1.04 (dd, J=7, 4 Hz, 2H).
Workup
- extractionextracted with dichloromethane (3×50 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationgravity-filtered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-ef25156e467244d5b8635a5b0d9f5d21
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604211B2
Reaction notes
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