Water → 3-Benzyloxy-2-methoxypropylthioalcohol

HRID 846970Notes

Reaction equation

HRID 846970 reaction equation
C([S:4][CH2:5][CH:6]([O:16][CH3:17])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C.C[O-].[Na+].CS(O)(=O)=[O:23].O>CO.C(OCC)(=O)C>[CH2:9]([O:8][CH2:7][CH:6]([O:16][CH3:17])[CH2:5][S:4][OH:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 10942334Sodium MethoxideHCID 198241381-Acetylthio-3-benzyloxy-2-methoxypropane

Product 1

HCID 198241363-Benzyloxy-2-methoxypropylthioalcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 14.028 g (55 mM) of acetylthio-3-benzyloxy-2-methoxypropane VII 6 in 300 ml of methanol is added dropwise 11.24 ml (58.3 mM) of 28 weight % solution of sodium methoxide in methanol at -10° C. After the mixture is stirred at -10° C. to 0° C. for 2 hours, 3.58 ml of methanesulfonic acid is added. The reaction mixture is poured into water and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with water, dried, and evaporated. The oily residue is purified by column chromatography on silica gel using an ether-n-hexane (3:97) mixture as an eluent to give 8.85 g (41.7 mM) of the titled compound, 3-benzyloxy-2-methoxypropylthioalcohol VII 6 as an oil.

Workup

  1. washThe ethyl acetate layer is washed with water
  2. customdried
  3. customevaporated
  4. customThe oily residue is purified by column chromatography on silica gel using an ether-n-hexane (3:97) mixture as an eluent

Sources & evidence

ORD record
ord-74fb6df58684465abe9a57db67532f6f
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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