Methanesulfonyl chloride → (1-Methylcyclopropyl)methyl methanesulfonate

HRID 715126Notes

Reaction equation

HRID 715126 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 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Treat a 0° C. solution of (1-methylcyclopropyl)methanol (1.0 g, 11.61 mmol) in DCM (50 mL) with TEA (1.29 g, 12.77 mmol), add methanesulfonyl chloride (1.46 g, 12.77 mmol) drop-wise and stir at 0° C. for 2 h. Warm the mixture to RT, wash with H2O, then brine, dry over Na2SO4 and concentrate to dryness to afford the title compound (1.85 g, 97%) as an oil. 1H NMR (400 MHz, DMSO-d6): δ 4.05 (s, 2H), 3.20 (s, 3H), 1.17 (s, 3H), 0.59 (m, 2H), 0.47 (m, 2H).

Workup

  1. temperatureWarm the mixture to RT
  2. washwash with H2O
  3. dry with materialbrine, dry over Na2SO4
  4. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-55dd982daedf406fa2a1f499ad158f9a
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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