Sodium borohydride → HCID 58188263, compound

HRID 1845138Notes

Reaction equation

HRID 1845138 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=1.[BH4-].[Na+]>CO>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58187990HCID 58187990, compound

Product 1

HCID 58188263HCID 58188263, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round bottom flask was charged with methyl-4-methyl-3-(methylsulfonyl)benzoate (1.5 g, 7.0 mmol) and methanol (15 mL) at 0° C. Sodium borohydride (3.7 g, 100 mmol) was added in portions and the reaction was stirred for 12 h at room temperature. The reaction was quenched with ice and extracted with MTBE. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography to get the title compound.

Workup

  1. customThe reaction was quenched with ice
  2. extractionextracted with MTBE
  3. concentrationThe combined organic phases were concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-56434e63417e49b0a988ef423117efaa
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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