Triethylamine → 1,3-Dimethoxypropan-2-yl methanesulfonate

HRID 2304265Notes

Reaction equation

HRID 2304265 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][CH2:8][CH:9]([OH:13])[CH2:10][O:11][CH3:12].C(N(CC)CC)C>ClCCl>[CH3:6][O:7][CH2:8][CH:9]([O:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121901,3-Dimethoxy-2-propanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 225957861,3-Dimethoxypropan-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.3 mL of methanesulfonyl chloride was added dropwise at 5° C. to a stirred solution of 6.0 g of 1,3-dimethoxy-propan-2-ol and 9.0 mL of triethylamine in 60 mL of dichloromethane. Stirring was continued for 72 hours at room temperature, followed by extraction with water. The combined organic extracts were dried (sodium sulfate) and concentrated and the residue purified by silica chromatography (isohexane/ethyl acetate=9/1, 8/2, 7/3, 6/4 v/v) yielding 2.5 g of methanesulfonic acid 2-methoxy-1-methoxymethyl-ethyl ester as an oil. EI-MS: 198 (M+).

Workup

  1. extractionfollowed by extraction with water
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. concentrationconcentrated
  4. customthe residue purified by silica chromatography (isohexane/ethyl acetate=9/1, 8/2, 7/3, 6/4 v/v)

Sources & evidence

ORD record
ord-35350037c1874ba980568d249faa06bf
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

Loading…