Sodium borohydride → (2s)-2-(4-Bromophenoxy)-3-methyl-1-butanol

HRID 380019Notes

Reaction equation

HRID 380019 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C@@H:9]([CH:14]([CH3:16])[CH3:15])[C:10](OC)=[O:11])=[CH:6][CH:5]=1>C(O)C>[Br:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C@@H:9]([CH:14]([CH3:16])[CH3:15])[CH2:10][OH:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131722884(2S)-2-(4-Bromophenoxy)-3-methylbutanoic acid, methyl ester

Product 1

HCID 57241843(2s)-2-(4-Bromophenoxy)-3-methyl-1-butanolYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid sodium borohydride (11.8 g) was added with cooling in three portions over 3 days to a stirred solution of (2S)-2-(4-bromophenoxy)-3-methylbutanoic acid, methyl ester (27.7 g) in ethanol (400 ml). The reaction was concentrated under reduced pressure and the residue partitioned between 2M hydrochloric acid (400 ml) and ether. The organic layer was dried over anhydrous magnesium sulfate filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluting with dichloromethane:isohexane (1:1) to give the sub-title compound as an oil (13.7 g).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue partitioned between 2M hydrochloric acid (400 ml) and ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel eluting with dichloromethane:isohexane (1:1)

Sources & evidence

ORD record
ord-4376fc0d82874755b9cd40a09d4edf4f
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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