Triethylamine → (2R)-Butan-2-YL methanesulfonate

HRID 348419

Reaction equation

HRID 348419 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[CH3:10][C@@H:11](O)[CH2:12][CH3:13].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:5][C@H:11]([CH3:10])[CH2:12][CH3:13])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 84682(-)-2-Butanol

Product 1

HCID 148500(2R)-Butan-2-YL methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonic anhydride (8.33 g, 47.8 mmol) in dichloromethane (30 ml) was added dropwise over 30 minutes to an ice-cooled solution of (R)-2-butanol (4.0 ml, 43.5 mmol) and triethylamine (6.65 ml, 47.8 mmol) in dichloromethane (70 ml). The reaction was then allowed to warm to room temperature and stirred for 18 hours. The mixture was then washed with water, 2N hydrochloric acid, then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a pale yellow oil, 7.0 g.

Workup

  1. washThe mixture was then washed with water, 2N hydrochloric acid
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-90301e4243ad4986aac61da05fd1e19a
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Linked notes

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