Sodium borohydride → 5-(Methylsulfonyl)[1,1'-biphenyl]-2-methanol

HRID 1499241Notes

Reaction equation

HRID 1499241 reaction equation
[Cl-].[Cl-].[Ca+2].[CH3:4][S:5]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:20](OC)=[O:21])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[BH4-].[Na+]>CCO.C1COCC1>[CH3:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([CH2:20][OH:21])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)(=[O:6])=[O:7]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 669687265-(Methylsulfonyl)biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 1179420385-(Methylsulfonyl)[1,1'-biphenyl]-2-methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of CaCl2 (1.52 g, 13.78 mmol) in EtOH (50 mL) at RT was added methyl 5-(methylsulfonyl)-[1,1′-biphenyl]-2-carboxylate (2 g, 6.9 mmol) in THF (50 mL) followed by the addition of NaBH4 (1.0 g, 27.6 mmol). The reaction was stirred at RT for 24 h, then concentrated in vacuo and extracted with ethyl acetate, 5% HCl, and brine. Purification on normal phase silica gel provided (5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)methanol as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate, 5% HCl, and brine
  3. customPurification on normal phase silica gel

Sources & evidence

ORD record
ord-fb349101b30e4bd7adc3eb33c00626e1
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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