Water → (2S)-3-phenylthio-1-tosyloxy-2-propanol

HRID 2299633Notes

Reaction equation

HRID 2299633 reaction equation
[S:1]([O:11][CH2:12][C@@H:13]1[O:15][CH2:14]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(N(CC)C(C)C)(C)C.[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>O1CCCC1>[C:25]1([S:31][CH2:14][C@@H:13]([OH:15])[CH2:12][O:11][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 13439563(2S)-3-phenylthio-1-tosyloxy-2-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, to a solution of (2R)-1-tosyloxy-2,3-epoxypropane (3.0 g) in tetrahydrofuran (30 ml) were added N,N-diisopropylethylamine (2.5 ml) and thiophenol (1.3 ml) at 5° C., and the mixture was stirred at room temperature for 12 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 3:1) to give (2S)-3-phenylthio-1-tosyloxy-2-propanol (3.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 3:1)

Sources & evidence

ORD record
ord-7e806c2d775448e9afc9cad6e9c7c74a
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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