Acetone → HCID 53761045, compound

HRID 1978262Notes

Reaction equation

HRID 1978262 reaction equation
[BH4-].[Na+].[CH3:3][C:4](=[CH:7][CH2:8][CH:9]1[CH2:14][CH:13]2[C:11]([CH3:15])([CH2:12]2)[C:10]1([CH3:17])[CH3:16])[CH:5]=[O:6].CC(C)=O>O.C(O)C>[CH3:3][C:4](=[CH:7][CH2:8][CH:9]1[CH2:14][CH:13]2[C:11]([CH3:15])([CH2:12]2)[C:10]1([CH3:17])[CH3:16])[CH2:5][OH:6]

Participants

6

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 54067917HCID 54067917, compound

Product 1

HCID 53761045HCID 53761045, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.5 g (10 mmol) of sodium borohydride dissolved in 5 ml of water was added portionwise to the solution of 5.0 g (24 mmol) of 2-methyl-4-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)but-2-enal in 20 ml of ethanol maintained at 0° C. Stirring was continued for 1 hour at 0-5° C., then acetone was added to destroy the excess of hydride. The reaction mixture was poured on 100 ml of water, extracted with 2×100 ml of ether, dried (MgSO4) and evaporated in vacuo. Kugelrohr distillation of the residue at 160° C./0.1 Torr gave 4.5 g (90% yield) of 2-methyl-4-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)but-2-en-1-ol.

Workup

  1. customto destroy the excess of hydride
  2. additionThe reaction mixture was poured on 100 ml of water
  3. extractionextracted with 2×100 ml of ether
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. distillationKugelrohr distillation of the residue at 160° C./0.1 Torr

Sources & evidence

ORD record
ord-c0e9124149d84c81a7c0ce6d3e259957
Source dataset
uspto-grants-2001_05
Patent number
US06235943B1

Reaction notes

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