8-Cyclohexadecen-1-one → HCID 53780017, compound

HRID 1941022Notes

Reaction equation

HRID 1941022 reaction equation
[Br-].[C:2]1([C:8]([PH3+])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)C=CC=CC=1.[CH2:22]([Li])[CH2:23][CH2:24]C.C1(=O)CCCCCCCC=CCCCCCC1>C(OCC)C>[CH2:2]=[C:8]1[CH2:9][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:24][CH:23]=[CH:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:15]1

Participants

5

Reactant 3

HCID 5346348-Cyclohexadecen-1-oneHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 53780017HCID 53780017, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10.7 g of triphenylmethylphosphonium bromide are added at room temperature to a mixture of 20 ml of n-butyllithium (1.55 molar in hexane) and 60ml of diethyl ether. After the mixture has been held at room temperature for 4 hours, 7.3 g of 8-cyclohexadecen-1-one are added dropwise, and the mixture is refluxed for 18 hours. After filtration, the solvent is removed by distillation, the residue is purified by chromatography (SiO2, hexane/ethyl acetate 95:5), giving 2.5 g of 1-methylene-8-cyclohexadecene, identified by a 1H-NMR spectrum:

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationAfter filtration
  3. customthe solvent is removed by distillation
  4. customthe residue is purified by chromatography (SiO2, hexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-01b42751f11f46838e891d7268d089e0
Source dataset
uspto-grants-1997_12
Patent number
US05702777

Reaction notes

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