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

HRID 2375284Notes

Reaction equation

HRID 2375284 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([OH:8])[CH2:5][O:6][CH3:7].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH:4]([O:8][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:5][O:6][CH3:7]

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

Procedure

To a solution of 1,3-dimethoxy-2-hydroxypropane (3.84 g, 0.032 mol) in DCM (70 ml) cooled at 5° C. was added triethylamine (5 ml, 0.036 mol) followed by slow addition of methanesulphonyl chloride (2.72 ml, 0.035 mol). The mixture was then stirred at ambient temperature for 24 hours. The mixture was then absorbed onto silica gel and purified by flash silica chromatography DCM:isohexane (3:1) 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 flash silica chromatography DCM:isohexane (3:1)

Sources & evidence

ORD record
ord-944346f22381416c9c0ae991aa1f560d
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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