Methoxymethyl-triphenylphosphonium chloride → HCID 178448047, compound

HRID 566165Notes

Reaction equation

HRID 566165 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[CH2:30]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C@H:39]2[CH2:44][CH2:43][C@H:42]([CH2:45][CH2:46][CH:47]=O)[CH2:41][CH2:40]2)[CH2:35][CH2:34]1)[CH2:31][CH3:32]>C1COCC1>[CH3:2][O:3][CH:4]=[CH:47][CH2:46][CH2:45][C@H:42]1[CH2:43][CH2:44][C@H:39]([C@H:36]2[CH2:37][CH2:38][C@H:33]([CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35]2)[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 178448051HCID 178448051, compound

Product 1

HCID 178448047HCID 178448047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A mixture of 57.3 g (167 mmol) of methoxymethyl-triphenylphosphonium chloride and 500 ml of THF was cooled to −30° C. under a nitrogen gas stream with a refrigeration medium. 17.3 g (154 mmol) of t-BuOK was added to this mixture, followed by stirring for 1 hour. To this mixture, 300 ml of THF containing 34.0 g (129 mmol) of 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanal was added dropwise, while a temperature of −30° C. or less was maintained. After the dropping, a reaction temperature was gradually raised to room temperature, followed by stirring for 5 hours. The reaction mixture was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was purified through silica gel column chromatography (a developing solvent: heptane) to obtain 30.3 g of crude 1-methoxy-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-butene.

Workup

  1. temperaturewas maintained
  2. temperatureAfter the dropping, a reaction temperature was gradually raised to room temperature
  3. stirringby stirring for 5 hours
  4. filtrationThe reaction mixture was filtered through Celite
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (a developing solvent

Sources & evidence

ORD record
ord-9d5cb03def2f4da5a6011fc2548822fa
Source dataset
uspto-grants-2001_01
Patent number
US06174459B1

Reaction notes

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