Sodium borohydride → 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol

HRID 1669329Notes

Reaction equation

HRID 1669329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:16].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 673424431-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one

Product 1

HCID 673450331-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-olYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one (3.5 g, 12.4 mmol) was dissolved in ethanol and cooled to 0° C. while stirring under nitrogen. To the flask was added sodium borohydride (469 mg, 12.4 mmol), and the reaction was kept at 0° C. for 1 h., then slowly warmed to room temperature. The reaction was monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with water, the ethanol removed by rotary evaporator, and extracted with diethyl ether, washed, dried, and concentrated. The title compound (3.33 g, 11.72 mmol), is used in the next step without further purification.

Workup

  1. temperatureslowly warmed to room temperature
  2. customUpon complete consumption of starting material
  3. customthe reaction is carefully quenched with water
  4. customthe ethanol removed by rotary evaporator
  5. extractionextracted with diethyl ether
  6. washwashed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-72b9b7aab46c4078a77272c2e0b35549
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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