Propyltriphenylphosphonium bromide → HCID 54378474, compound

HRID 1106363Notes

Reaction equation

HRID 1106363 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1.[Br-].[CH2:14]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:15][CH3:16].CC(C)([O-])C.[K+]>C1COCC1>[CH:14](=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 80374Propyltriphenylphosphonium bromideHCID 21249113Methyl 2-(4-oxocyclohexyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54378474HCID 54378474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

64.4 g of methyl (4-oxocyclohexyl)acetate and 137.9 g of propyltriphenylphosphonium bromide were introduced into 500 ml of THF, and the mixture was cooled to -10° C. with stirring under nitrogen. A solution of 40.17 g of potassium tert-butoxide in 400 ml of THF was then added dropwise with stirring at the same temperature, and the mixture was then stirred at RT for a further 2 h. Conventional work-up gave methyl (4-propylidenecyclohexyl)acetate.

Workup

  1. stirringwith stirring at the same temperature
  2. stirringthe mixture was then stirred at RT for a further 2 h

Sources & evidence

ORD record
ord-11cdcab87a3d488a90e3287eb50c272d
Source dataset
uspto-grants-2000_05
Patent number
US06056895

Reaction notes

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