Tetrahydrofuran → HCID 178445630, compound

HRID 567624Notes

Reaction equation

HRID 567624 reaction equation
[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[CH2:30]([C@H:34]1[CH2:39][CH2:38][C@H:37]([C@H:40]2[CH2:45][CH2:44][C@H:43](CC=O)[CH2:42][CH2:41]2)[CH2:36][CH2:35]1)[CH2:31][CH:32]=[CH2:33].[CH2:49]1[CH2:53][O:52][CH2:51][CH2:50]1>>[CH3:51][O:52][CH2:53][CH:49]=[CH:50][C@H:43]1[CH2:44][CH2:45][C@H:40]([C@H:37]2[CH2:36][CH2:35][C@H:34]([CH2:30][CH2:31][CH:32]=[CH2:33])[CH2:39][CH2:38]2)[CH2:41][CH2:42]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 178445632HCID 178445632, compound

Product 1

HCID 178445630HCID 178445630, compound

Conditions

Temperature
-50 °C

Procedure

A mixture of 25.2 g (73.5 mmol) of methoxymethyltriphenyl phosphonium chloride and 300 ml of THF was cooled to −50° C. under a gas stream of nitrogen. To the mixture, 7.6 g (67.8 mmol) of t-BuOK was added and stirred for 1 hour. To the mixture, a solution of 14.8 g (56.5 mmol) of trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl acetaldehyde in 150 ml of THF was added dropwise with maintaining the temperature below −50° C. After dropwise addition, the reaction temperature was increased gradually to the room temperature, and stirring was carried out further for 5 hours. The solvent was distilled off under a decresed pressure, 150 ml of water was added and the mixture was extracted with 200 ml of toluene. The organic layer was washed with 100 ml of water for three times and dried with anhydrous magnesium sulphate. The solvent was distilled off under a decreased pressure, and the residue was subjected to silica gel column chromatography (eluent: a mixed solvent of toluene/heptane=3/7), to obtain 12.8 g of crude 1-(3-methoxypropenyl)-trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexane.

Workup

  1. temperaturewith maintaining the temperature below −50° C
  2. additionAfter dropwise addition
  3. temperaturethe reaction temperature was increased gradually to the room temperature
  4. stirringstirring
  5. waitwas carried out further for 5 hours
  6. distillationThe solvent was distilled off under a decresed pressure, 150 ml of water
  7. additionwas added
  8. extractionthe mixture was extracted with 200 ml of toluene
  9. washThe organic layer was washed with 100 ml of water for three times
  10. dry with materialdried with anhydrous magnesium sulphate
  11. distillationThe solvent was distilled off under a decreased pressure

Sources & evidence

ORD record
ord-e9d82eb5404043f19eaccd8191814f5f
Source dataset
uspto-grants-2001_01
Patent number
US06180027B2

Reaction notes

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