Sodium borohydride → 5-Methylcyclodec-5-en-1-one

HRID 905133Notes

Reaction equation

HRID 905133 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([CH:11]=[CH2:12])[OH:10])([CH3:3])=[CH2:2].[BH4-].[Na+]>C(Cl)Cl.[OH-].[Na+]>[CH3:3][C:1]1[CH2:2][CH2:12][CH2:11][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12677739HCID 12677739, compound

Product 1

HCID 538872325-Methylcyclodec-5-en-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-isopropenyl-1-vinylcyclohexan-1-ol (0.166 g, 10-3 mol) and mercuric trifluoroacetate (0.423 g) in methylene chloride (10 cc) is kept at a temperature of the order of 20° C. After a reaction time of 5 minutes, a solution of sodium borohydride (0.010 g) in 3 N sodium hydroxide solution (0.66 cc) is added to the reaction mixture. The reaction mixture is extracted with methylene chloride (3×10 cc). The organic extracts are dried over magnesium sulphate. After filtration and concentration of the solvent under reduced pressure (20 mm Hg; 2.7 kPa), 5-methylcyclodec-5-en-1-one (0.024 g) is obtained, the characteristics of which are as follows: Infra-red spectrum of a liquid film: characteristic bands at 2980 and 1710 cm-1 ;

Workup

  1. customis kept at a temperature of the order of 20° C
  2. extractionThe reaction mixture is extracted with methylene chloride (3×10 cc)
  3. dry with materialThe organic extracts are dried over magnesium sulphate
  4. filtrationAfter filtration and concentration of the solvent under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-81d19300af144d6792617c47ecf4bc22
Source dataset
uspto-grants-1983_12
Patent number
US04421934

Reaction notes

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