Methanesulfonyl chloride → (1-Methylcyclopropyl)methyl methanesulfonate

HRID 522718Notes

Reaction equation

HRID 522718 reaction equation
[CH3:1][C:2]1([CH2:5][OH:6])[CH2:4][CH2:3]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9]>C(Cl)Cl>[CH3:7][S:8]([O:6][CH2:5][C:2]1([CH3:1])[CH2:4][CH2:3]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 137701(1-Methylcyclopropyl)methanol

Product 1

HCID 13638452(1-Methylcyclopropyl)methyl methanesulfonateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Treat a cooled solution (0° C.) of 1-methylcyclopropanemethanol (2.0 g, 23.22 mmol) in DCM (75 mL) with TEA (2.58 g, 25.5 mmol) and add methanesulfonyl chloride (2.93 g, 25.5 mmol) dropwise. Stir the mixture at 0° C. for 2 h, wash with H2O then brine, dry over Na2SO4 and concentrate to dryness to afford the title compound (3.66 g, 96%) as an oil. 1H NMR (400 MHz, DMSO-d6): δ 3.60 (s, 3H), 2.10 (m, 2H), 0.72 (s, 3H), 0.14 (m, 2H), 0.01 (m, 2H).

Workup

  1. washwash with H2O
  2. dry with materialbrine, dry over Na2SO4
  3. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-8f9522bda5f74728bf876b0552e60e0f
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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