Water → HCID 178455764, compound

HRID 726449Notes

Reaction equation

HRID 726449 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[CH3:28][O:29][C:30]([C@H:32]1[CH2:37][CH2:36][C@H:35]([C@H:38]2[CH2:43][CH2:42][C@H:41]([C@H:44]3[CH2:49][CH2:48][C@H:47]([CH:50]=O)[CH2:46][CH2:45]3)[CH2:40][CH2:39]2)[CH2:34][CH2:33]1)=[O:31].O>C1COCC1>[CH3:28][O:29][C:30]([C@H:32]1[CH2:37][CH2:36][C@H:35]([C@H:38]2[CH2:39][CH2:40][C@H:41]([C@H:44]3[CH2:49][CH2:48][C@H:47]([CH:50]=[CH2:2])[CH2:46][CH2:45]3)[CH2:42][CH2:43]2)[CH2:34][CH2:33]1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 178501096HCID 178501096, compound

Product 1

HCID 178455764HCID 178455764, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

A mixture of 30.2 g (74.7 mmol) of methyltriphenylphosphonium iodide and 400 ml of THF was cooled to -50° C. To this mixture was added 9.23 g (82.2 mmol) of t-BuOK and the resulting mixture was stirred for one hour. To this mixture was added dropwise a solution of 20.0 g (59.8 mmol) of trans-4-(trans-4-(trans-4-formylcyclohexyl)cyclohexyl)cyclohexane carboxylic acid methyl ester in 500 ml of THF, while maintaining a temperature at below -50° C. After the dropwise addition, the reaction temperature was gradually allowed to rise up to room temperature. After 300 ml of water was added to the reaction mixture, the reaction mixture was extracted with 1000 ml of toluene. The organic layer was washed three times with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to a silica gel column chromatography (a developing solvent: heptane) to give 9.90 g of crude trans-4-(trans-4-(trans-4-ethenylcyclohexyl)cyclohexyl)-cyclohexane carboxylic acid methyl ester.

Workup

  1. temperaturewhile maintaining a temperature at below -50° C
  2. additionAfter the dropwise addition
  3. customto rise up to room temperature
  4. extractionthe reaction mixture was extracted with 1000 ml of toluene
  5. washThe organic layer was washed three times with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cf5e2a0db7d1490887fed64f877322f2
Source dataset
uspto-grants-1998_01
Patent number
US05709820

Reaction notes

Loading…