Triethylamine → Cyclopropylmethyl methanesulfonate
Reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[CH3:6][S:7](Cl)(=[O:9])=[O:8].C(N(CC)CC)C>CCOCC>[CH3:6][S:7]([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)(=[O:9])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Cyclopropylcarbinol (27.4 g; 0.373 mol) and methanesulfonyl chloride (47.56 g; 0.407 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (59 ml; 0.42 mol) is added dropwise over 45 min with external cooling so that the reaction temperature remained below -15° C. The reaction mixture was allowed to warm to room temperature over 2 h and then filtered. The solid material is washed with ether. The solutions were combined and evaporated, to afford crude cyclopropylmethyl methanesulfonate (58.36 g) as a pale yellow liquid, which was used without further purification. NMR - d(CDCl3 ; 60 MHz) 0.3-1.5 (5H, m), 3.0 (3H, s) and 4.0 (2H, d, J=7 Hz).