Water → HCID 22841017, compound

HRID 414781Notes

Reaction equation

HRID 414781 reaction equation
C[O-].[Na+].[CH2:4]([O:11][CH2:12][C@H:13]1[C@@H:18]([S:19]C(=O)C)[CH2:17][CH2:16][CH2:15][O:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CS(O)(=O)=O.O>CO>[CH2:4]([O:11][CH2:12][C@H:13]1[C@@H:18]([SH:19])[CH2:17][CH2:16][CH2:15][O:14]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=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 a methanolic solution containing about 28% w/w of sodium methoxide was added dropwise at -10° C. to a solution of 1.422 g of dl-cis-2-benzyloxymethyl-3-acetylthiotetrahydropyran (prepared as described in Preparation 15) in 30 ml of methanol. The reaction mixture was stirred at between -10° and 0° C. for 2 hours, after which 0.33 ml of methanesulfonic acid was added. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated by evaporation under reduced pressure. The oily residue thus obtained was subjected to column chromatography through 30 g of silica gel. The fraction eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 5:95 by volume was collected to give 1.146 g of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe oily residue thus obtained
  6. washThe fraction eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 5:95 by volume
  7. customwas collected

Sources & evidence

ORD record
ord-66177f804b2449fc88edb5fc557e87cc
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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