Diisoamyl ketone → 2,8-Dimethyl-5-nonanol

HRID 847595Notes

Reaction equation

HRID 847595 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][C:6](=[O:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:3].[BH4-].[Na+]>CO>[CH3:3][CH:2]([CH2:4][CH2:5][CH:6]([OH:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:1]

Participants

4

Reactant 2

HCID 62421Diisoamyl ketoneHCID 4311764Sodium borohydride

Product 1

HCID 5578512,8-Dimethyl-5-nonanolYield 40.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.63 g (33 mmol) of 2,8-dimethylnonan-5-one in 150 ml of methanol was cooled to 0° C. and treated with 0.8 g (21 mmol) of sodium borohydride. After 1 h, the solution was quenched with 1N HCl; diluted with 1:1 hexane/ether; washed sequentially with 1N NaOH, water, and saturated brine; dried over MgSO4 ; and concentrated in vacuo. Flash chromatography using 10% ethyl acetate in hexane gave 2.30 g (40%) of the desired compound (Rf 0.36, 20% ethyl acetate in hexane) as a colorless oil. 1H NMR (CDCl3) 0.88 (d, J=7 Hz, 6H), 0.89 (d, J=7 Hz, 6H), 1.1-1.6 (m, 10H), 3.56 (m, 1H).

Workup

  1. customthe solution was quenched with 1N HCl
  2. additiondiluted with 1:1 hexane/ether
  3. washwashed sequentially with 1N NaOH, water, and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationand concentrated in vacuo

Sources & evidence

ORD record
ord-d6bfcaa77b574829bd894d8382d9f453
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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