Sodium borohydride → HCID 15541122, compound

HRID 1979141Notes

Reaction equation

HRID 1979141 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 14116665HCID 14116665, compound

Product 1

HCID 15541122HCID 15541122, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of sodium borohydride (0.0376 g, 0.00099 mol) in absolute ethanol under nitrogen at room temperature was added in one portion 4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid (0.576 g, 0.00199 mol), and the mixture stirred for 4 hours. Additional sodium borohydride (0.013 g, 0.00034 mol) was added, and the mixture stirred for 18 hours. Additional sodium borohydride (0.0144 g, 0.000381 mol) was added and the mixture stirred for 5 hours. Total reaction time was 27 hours. The reaction was quenched with acetone-water and partitioned between 1 M hydrochloric acid and dichloromethane. The organic layer was washed with brine, dried (Na2SO4), and rotary evaporated. The residue was purified by chromatography on silica gel using dichloromethane-methanol (19:1, 1.3 L; 15:1, 1.3 L) to give 0.101 g of (±)-4-(4′-chloro-biphenyl-4-yl)-4-hydroxy-butyric acid as a white solid; mp 133.5-135.0° C.

Workup

  1. stirringthe mixture stirred for 18 hours
  2. stirringthe mixture stirred for 5 hours
  3. waitTotal reaction time was 27 hours
  4. customThe reaction was quenched with acetone-water
  5. custompartitioned between 1 M hydrochloric acid and dichloromethane
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4), and rotary evaporated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6768fae44e894691a3551d406bdcc009
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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