Methoxymethyl-triphenylphosphonium chloride → HCID 178448047, compound

HRID 989579Notes

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

Conditions

Temperature: -30 °C

Procedure

Under nitrogen gas stream, a mixture of 405 g (1180 mmol) of methoxymethyltriphenylphosphonium chloride with 4.0 l of THF was cooled down to −30° C., 122 g (1090 mmol) of t-BuOK was added thereto, and they were stirred for 1 hour. To this mixture was added by drops a solution of 240 g (907 mmol) of the crude 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanal in 2.4 l of THF while being maintained at a temperature lower than −30° C. After finishing of the dropping, the reaction temperature was gradually raised up to room temperature, and the mixture was stirred for further 5 hours. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: heptane) to obtain 152 g of a crude 1-methoxy-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)butene.

Workup

temperaturewhile being maintained at a temperature lower than −30° C
temperaturethe reaction temperature was gradually raised up to room temperature
stirringthe mixture was stirred for further 5 hours
filtrationThe reaction mixture was filtered with Celite
distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record: ord-9c9269f559a742a4b52f191fe1916773
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458433B1

Reaction notes

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