Water → HCID 178447970, compound

HRID 342362Notes

Reaction equation

HRID 342362 reaction equation
[Br-].[Cl:2][C:3]1[CH:28]=[CH:27]C(C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[CH3:29][C:30](C)([O-])C.[K+].[CH2:35]([C@H:38]1[CH2:43][CH2:42][C@H:41]([CH2:44][CH2:45][C@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]3[CH:59]=[CH:58][CH:57]=[CH:56][C:53]=3[CH:54]=O)[CH2:48][CH2:47]2)[CH2:40][CH2:39]1)[CH2:36][CH3:37].O>C1COCC1>[CH2:35]([C@H:38]1[CH2:43][CH2:42][C@H:41]([CH2:44][CH2:45][C@H:46]2[CH2:47][CH2:48][C@H:49]([C:52]3[CH:30]=[CH:29][C:57]([CH:56]=[CH:53][C:54]4[CH:27]=[CH:28][C:3]([Cl:2])=[CH:4][CH:5]=4)=[CH:58][CH:59]=3)[CH2:50][CH2:51]2)[CH2:40][CH2:39]1)[CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 11102709T0400-2412HCID 23665647Potassium tert-butoxideHCID 178447968HCID 178447968, compound

Product 1

HCID 178447970HCID 178447970, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Suspension of 10.7 g of 4-chlorobenzyltriphenyl phosphonium bromide in 100 ml of THF was stirred under nitrogen gas stream and 2.5 g of potassium-t-butoxide was added thereto at room temperature. After stirred at room temperature for 1 hour, a solution prepared by dissolving 6 g of the (trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzaldehyde mentioned above in 50 ml of THF was added dropwise. After stirred at room temperature for 2 hours, 300 ml of water was added and extracted with 300 ml of ethyl acetate. Organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and then 250 ml of heptane was added thereto. Precipitate thus separated was filtered off and purified by a column chromatography over silica gel by using ethyl acetate/heptane (1/5) as an eluent. Solvent was distilled off under a reduced pressure to obtain 5.4 g of 4-(2-(4-(trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)phenyl)ethenyl)chlorobenzene.

Workup

  1. additionwas added
  2. customat room temperature
  3. customa solution prepared
  4. additionwas added dropwise
  5. stirringAfter stirred at room temperature for 2 hours
  6. extractionextracted with 300 ml of ethyl acetate
  7. washOrganic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under a reduced pressure
  10. addition250 ml of heptane was added
  11. customPrecipitate thus separated
  12. filtrationwas filtered off
  13. custompurified by a column chromatography over silica gel
  14. distillationSolvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-8f017bc054cd4f059ffc174582d3a378
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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