Ethanol → 10-Ethoxy-6,10-dimethylundec-3-en-2-one

HRID 918326Notes

Reaction equation

HRID 918326 reaction equation
[CH3:1][CH:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH2:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7].[OH-].[K+].[BH4-].[Na+].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:12]([CH3:13])([CH3:14])[CH2:11][CH2:10][CH2:9][CH:2]([CH3:1])[CH2:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7])[CH3:20]

Participants

5

Reactant 4

HCID 702Ethanol3×HCID 14797Potassium HydroxideHCID 1171636,10-Dimethylundeca-3,9-dien-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 5375466210-Ethoxy-6,10-dimethylundec-3-en-2-one

Procedure

To a solution of 1.8 g. of 6,10-dimethylundeca-3,9-dien-2-one in 20 ml. of ethanol, cooled to 0° by an ice bath is added a suspension of 2.32 g. of mercuric acetate in 50 ml. of ethanol over 15 minutes. The reaction mixture is stirred for 2 hours and then, with cooling, to -20°, 1.22 g. of potassium hydroxide in 20 ml. of ethanol is added. Then 0.139 g. of sodium borohydride is added in small portions and stirring continued for 30 minutes at -20°. The solution is decanted, then concentrated to half volume, diluted with 100 ml. of water and extracted with ether (3 × 50). The ethereal phase is washed with water, dried over magnesium sulfate and the crude product chromatographed on silica to yield 10-ethoxy-6,10-dimethylundec-3-en-2-one.

Workup

  1. additionis added
  2. additiona suspension of 2.32 g
  3. temperaturewith cooling, to -20°
  4. stirringstirring
  5. waitcontinued for 30 minutes at -20°
  6. customThe solution is decanted
  7. concentrationconcentrated to half volume
  8. additiondiluted with 100 ml
  9. extractionof water and extracted with ether (3 × 50)
  10. washThe ethereal phase is washed with water
  11. dry with materialdried over magnesium sulfate
  12. customthe crude product chromatographed on silica

Sources & evidence

ORD record
ord-3945b163ffc84898ac570d41e8200a1c
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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