Sodium borohydride → 3-(3-Bromophenyl)4-(4-chlorophenyl)-3-methyl-2-butanol

HRID 30359Notes

Reaction equation

HRID 30359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:20])([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:20])([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH:9]([OH:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 686756483-(3-Bromophenyl)-4-(4-chlorophenyl)-3-methyl-2-butanone

Product 1

HCID 686752163-(3-Bromophenyl)4-(4-chlorophenyl)-3-methyl-2-butanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(3-bromophenyl)4-(4-chlorophenyl)-3-methyl-2-butanone (1.6 g, 4.6 mmol) in methanol (50 mL) was added sodium borohydride (0.26 g, 6.8 mmol). After stirring at room temperature for 10 min, the reaction was quenched by addition of saturated aqueous ammonium chloride (25 mL). The precipitate was filtered off and washed with ethyl acetate (25 mL). The organic layer of the filtrate was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography on silica gel eluted with 5% ethyl acetate in hexane to afford the title compound as two separate diastereomers. Faster eluting diastereomer (Diastereomer α) 1H NMR (400 MHz, CD3OD): δ 7.63 (s, 1H), 7.42-7.18 (m, 3H), 7.05 (d, 2H), 6.80 (d, 2H), 3.92 (q, 1H), 3.19 (d, 1H), 2.86 (d, 1H), 1.13 (s, 3H), 1.02 (d, 3H). Slower eluting diastereomer (Diastereomer β) 1H NMR (400 MHz, CD3OD): 7.40-7.18 (m, 4H), 7.04 (d, 2H), 6.64 (d, 2H), 4.12 (q, 1H), 3.04 (ABq, 2H), 1.17 (s, 3H), 0.84 (d, 3H).

Workup

  1. customthe reaction was quenched by addition of saturated aqueous ammonium chloride (25 mL)
  2. filtrationThe precipitate was filtered off
  3. washwashed with ethyl acetate (25 mL)
  4. customThe organic layer of the filtrate was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c1d04b70e308420690a1a7ada8bac681
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

Loading…