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

HRID 1760510Notes

Reaction equation

HRID 1760510 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][CH2:15][CH:16]([OH:20])[CH2:17][O:18][CH3:19]>ClCCl>[CH3:13][O:14][CH2:15][CH:16]([O:20][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:17][O:18][CH3:19]

Participants

5

Reactant 3

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

Product 1

HCID 225957861,3-Dimethoxypropan-2-yl methanesulfonateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Triethylamine (5 ml, 0.036 mol) followed by slow addition of methanesulphonyl chloride (2.72 ml, 0.035 mol) was added to a solution of 1,3-dimethoxy-2-hydroxypropane (3.84 g, 0.032 mol) in dichloromethane (70 ml) cooled at 5° C. The mixture was then stirred at ambient temperature for 24 hours. The mixture was then absorbed onto silica gel and purified by chromatography eluting with dichloromethane/isohexane (1:1) to give the title compound (3.74 g, 59%). NMR: 3.15 (s, 3H), 3.28 (s, 6H), 3.52 (d, 4H), 4.78 (q, 1H).

Workup

  1. customThe mixture was then absorbed onto silica gel
  2. custompurified by chromatography
  3. washeluting with dichloromethane/isohexane (1:1)

Sources & evidence

ORD record
ord-269732a89eed4c9090886cb17497ba6b
Source dataset
uspto-grants-2005_01
Patent number
US06844341B2

Reaction notes

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