Sodium borohydride → 5-Cyclohexadecen-1-one

HRID 905134Notes

Reaction equation

HRID 905134 reaction equation
[CH:1]([C:3]1([OH:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH:15]=[CH2:16])=[CH2:2].[BH4-].[Na+]>C(Cl)Cl.[OH-].[Na+]>[C:3]1(=[O:17])[CH2:1][CH2:2][CH2:16][CH2:15][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11096619Cyclododecanol, 1,2-diethenyl-

Product 1

HCID 1622685-Cyclohexadecen-1-oneYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1,2-divinylcyclododecan-1-ol (0.125 g, 5.10-4 mol) and mercuric trifluoroacetate (0.215 g) in methylene chloride (4 cc) is kept at a temperature of the order of 20° C. After a reaction time of 1 hour 30 minutes, a solution of sodium borohydride (0.005 g) in 3 N sodium hydroxide solution (0.33 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), cyclohexadec-5-en-1-one (0.087 g) is obtained with a yield of 70%.

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-2008c3df562b4eb1be52ab227927b36c
Source dataset
uspto-grants-1983_12
Patent number
US04421934

Reaction notes

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