Sodium borohydride → HCID 15541122, compound

HRID 381822Notes

Reaction equation

HRID 381822 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 (Na2DO4), 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. customdried (Na2DO4), and rotary evaporated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-915ab592411146a5acc12c139d1b7570
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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