Water → (3-Methanesulfonylphenyl)methanol

HRID 1046356Notes

Reaction equation

HRID 1046356 reaction equation
[BH4-].[Na+].[CH3:3][S:4]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])(=[O:6])=[O:5].O>C(O)C>[CH3:3][S:4]([C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1)(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 135966023-(Methylsulfonyl)benzaldehyde

Product 1

HCID 23549738(3-Methanesulfonylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 is added to a solution of 750 mg (4.08 mmol) 3-methanesulphonyl-benzaldehyde in 20 ml ethanol (see P. L. Ornstein, T. J. Bleisch, M. B. Arnold, R. A. Wright, B. G. Johnson, J. P. Tizzano, D. R. Helton, M. J. Kallman, D. D. Schoepp, M. Herin, J. Med. Chem. 1998, 41(3), 358-378 or B. Eistert, W. Schade, H. Selzer, Ber. 1964, 97(5), 1470-81). The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is poured into water and extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, used in the next step without further purification.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers are washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4b5f717059e41d6a68257688faed29d
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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