Reaction #1792

ord-a131d665a87f4613af62e1177a8607d3

Reaction equation

O=C1C=COC(=S(=O)=O)C1
sulfonylpyran-4-one
[BH4-].[Na+]
NaBH4
→
O=S(=O)=c1cc(O)cco1
sulfonylpyran-4-ol

Reactants

O=C1C=COC(=S(=O)=O)C1
sulfonylpyran-4-one
[BH4-].[Na+]
NaBH4

Reagents

None

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was removed under reduced pressure
  2. 2
    Otherthe crude oil was chromatographed on a silica gel column
  3. 3
    Washhexanes and eluted with same
  4. 4
    Otherthe solvent was removed under reduced pressure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726172uspto-grants-1998_03