Sodium borohydride → 1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethane-1,2-diol

HRID 2377007Notes

Reaction equation

HRID 2377007 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:28])[CH2:26][OH:27])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH:25]([OH:28])[CH2:26][OH:27])(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 210993881-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]-2-hydroxyethanone

Product 1

HCID 210993891-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]-2-hydroxyethanone (Example 167, 20 mg, 0.05 mmol) and sodium borohydride (10 mg, 0.26 mmol) in methanol (2 mL) and dichloromethane (0.5 mL) was stirred at room temperature for 30 minutes. The reaction was quenched with water and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. δH (500 MHz, d6 DMSO): 8.04 (1H, d, J=7.9 Hz), 7.84-7.79 (4H, m), 7.74 (1H, d, J=7.7 Hz), 7.70-7.67 (3H, m), 7.53 (1H, t, J=7.3 Hz), 7.44 (1H, d, J=16.3 Hz), 7.29 (1H, d, J=16.4 Hz), 7.23 (2H, t, J=8.6 Hz), 5.36 (2H, s), 4.71 (1H, s), 3.32 (1H, s), 3.17 (1H, s).

Workup

  1. customThe reaction was quenched with water
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2508b529ebb343109263ab25bca3d152
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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