Triethylamine → Cyclopropylmethyl methanesulfonate

HRID 1032900Notes

Reaction equation

HRID 1032900 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

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 75644Cyclopropanemethanol

Product 1

HCID 135444Cyclopropylmethyl methanesulfonateYield 104.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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).

Workup

  1. temperaturewith external cooling so that the reaction temperature
  2. customremained below -15° C
  3. filtrationfiltered
  4. washThe solid material is washed with ether
  5. customevaporated

Sources & evidence

ORD record
ord-bf6ec68de33642ea8225a76689be6fe0
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

Loading…