Sodium borohydride → Sulfonylpyran-4-ol

HRID 1696

Reaction equation

HRID 1696 reaction equation
[S:1](=[C:4]1[CH2:9][C:8](=[O:10])[CH:7]=[CH:6][O:5]1)(=[O:3])=[O:2].[BH4-].[Na+]>CO>[S:1](=[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][O:5]1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19691003Sulfonylpyran-4-one

Product 1

HCID 19690976Sulfonylpyran-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of sulfonylpyran-4-one (1.2 g, 8.1 mmol) in MeOH (20 mL) was cooled to 0° C. under Argon and treated with NaBH4 (331 mg, 9.0 mmol). The reaction was stirred over 16 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil was chromatographed on a silica gel column packed in 50:50 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give the sulfonylpyran-4-ol.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude oil was chromatographed on a silica gel column
  3. washhexanes and eluted with same
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a131d665a87f4613af62e1177a8607d3
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

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