Sodium borohydride → 2-(4-Bromophenyl)-1-(4-chlorophenyl)pentan-1-ol

HRID 919029Notes

Reaction equation

HRID 919029 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:20][CH2:21][CH3:22])[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1>CO>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:20][CH2:21][CH3:22])[CH:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[OH:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670163502-(4-Bromophenyl)-1-(4-chlorophenyl)pentan-1-one

Product 1

HCID 670164322-(4-Bromophenyl)-1-(4-chlorophenyl)pentan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (917 mg, 24.25 mmol) was added to a MeOH solution (25 ml) containing the intermediate from Step C (6.53 g, 18.66 mol). After stirring for 1 hour at room temperature the solution was concentrated and the residue partitioned between water and EtOAc. The organic phase was washed with water, brine and dried over Na2SO4. The filtered solution was concentrated to give the title compound as an 8:1 mixture of diastereomers which was used in the next step without further purification. 1H NMR for major diastereomer (500 MHz, CDCl3): δ 7.44 (d, J=8.1 Hz, 2H); 7.30 (d, J=8.5 Hz, 2 H); 7.19 (d, J=8.5 Hz, 2 H); 7.07 (d, J=8.1 Hz, 2 H); 4.71-4.68 (m, 1 H); 2.81-2.74 (m, 1 H); 1.56-1.48 (m, 1 H); 1.42-1.32 (m, 1 H); 1.12-0.95 (m, 2H); 0.75 (t, J=7.3 Hz, 3 H). LC1 4.00 min. (M−OH)=335

Workup

  1. concentrationwas concentrated
  2. customthe residue partitioned between water and EtOAc
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-75beaa093c1b4ede9eb9cfb0d3a31011
Source dataset
uspto-grants-2016_03
Patent number
US09272999B2

Reaction notes

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