Water → 3-Benzyloxy-2-methoxy-1-methanesulphonyloxy-propane

HRID 1197159Notes

Reaction equation

HRID 1197159 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([O:13][CH3:14])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(OCC)C.ClCCl>[CH2:1]([O:8][CH2:9][CH:10]([O:13][CH3:14])[CH2:11][O:12][S:23]([CH3:22])(=[O:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1294271-O-benzyl-2-O-methylglycerol

Product 1

HCID 198978433-Benzyloxy-2-methoxy-1-methanesulphonyloxy-propaneYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.88 g (30 mmol) of 3b and 10 ml of triethylamine in 100 ml of dry diethyl ether and 50 ml of dichloromethane, was added under stirring 6.84 g (60 mmol) of methanesulphonyl chloride in 50 ml of dichloromethane, and the mixture was refluxed for 5 hours. Water was then added, and the organic phase was decanted, dried and evaporated. The crude product was chromatographed (eluent petroleum ether/diethyl ether 80:20 by volume), to yield 6 g (74%) of 4b.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customthe organic phase was decanted
  3. customdried
  4. customevaporated
  5. customThe crude product was chromatographed (eluent petroleum ether/diethyl ether 80:20 by volume)

Sources & evidence

ORD record
ord-d1d58a897053484897a9f277068f09fc
Source dataset
uspto-grants-1992_05
Patent number
US05116992

Reaction notes

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