Water → HCID 22841017, compound

HRID 329511Notes

Reaction equation

HRID 329511 reaction equation
C[O-].[Na+].C([S:7][C@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@H:9]1[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C.CS(O)(=O)=O.O>CO>[CH2:16]([O:15][CH2:14][C@H:9]1[C@@H:8]([SH:7])[CH2:13][CH2:12][CH2:11][O:10]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 10942334Sodium MethoxideHCID 22841013HCID 22841013, compound

Product 1

HCID 22841017HCID 22841017, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.04 ml of an approximately 28% w/v methanolic solution of sodium methoxide was added dropwise at -10° C. to 1.422 g of dl-S-(cis-2-benzyloxymethyltetrahydropyran-3-yl) thioacetate (prepared as described in Preparation 38) dissolved in 30 ml of methanol. The reaction mixture was stirred at -10° to 0° C. for 2 hours, and then 0.33 ml of methanesulfonic acid was added. The reaction mixture was then poured into water and extracted with ethyl acetate. The extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure to give an oily residue. The residue was subjected to column chromatography through 30 g of silica gel. Those fractions eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 5:95 by volume were worked up, to give 1.146 g of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customto give an oily residue
  6. washThose fractions eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 5:95 by volume

Sources & evidence

ORD record
ord-393b35149c0c4ed3aeab29fb50a968c6
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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