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

HRID 1769929Notes

Reaction equation

HRID 1769929 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 triphenylmethylphosphoniumbromide are added at room temperature to a mixture of 20 ml of n-butyllithium (1.55 molar in hexane) and 60 ml of diethyl ether. After the mixture has been kept 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. The mixture is filtered, the solvent is removed by distillation, and the residue is purified by chromatography (SiO2, hexane/ethyl acetate 95:5), giving 2.5 g of 1-methylene-8-cyclohexadecene, identified from the 1H-NMR spectrum: δ=5.2 (t, --CH=CH--); δ=4.75 (s, C=CH2).

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationThe mixture is filtered
  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-edf3e205246a4081b20d4c19e8fc26bb
Source dataset
uspto-grants-1995_01
Patent number
US05384168

Reaction notes

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