Water → HCID 178439112, compound

HRID 342359Notes

Reaction equation

HRID 342359 reaction equation
[Br-].[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[CH2:35]([C:38]1[CH:43]=[CH:42][C:41]([C@H:44]2[CH2:49][CH2:48][C@H:47]([CH2:50][CH2:51][C:52]3[CH:59]=[CH:58][C:55]([CH:56]=O)=[CH:54][CH:53]=3)[CH2:46][CH2:45]2)=[CH:40][CH:39]=1)[CH2:36][CH3:37].O>C1COCC1>[CH2:35]([C:38]1[CH:43]=[CH:42][C:41]([C@H:44]2[CH2:45][CH2:46][C@H:47]([CH2:50][CH2:51][C:52]3[CH:53]=[CH:54][C:55]([CH:56]=[CH:7][C:6]4[CH:5]=[CH:4][C:3]([Cl:2])=[CH:28][CH:27]=4)=[CH:58][CH:59]=3)[CH2:48][CH2:49]2)=[CH:40][CH:39]=1)[CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 11102709T0400-2412HCID 23665647Potassium tert-butoxideHCID 178439113HCID 178439113, compound

Product 1

HCID 178439112HCID 178439112, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Suspension of 11.8 g of 4-chlorobenzyltriphenyl-phosphonium bromide in 100 ml of THF was stirred under nitrogen gas stream, and 2.8 g of potassium-t-butoxide was added to the suspension at room temperature. After stirred at room temperature for 1 hour, a solution of 7 g of the 4-(2-(trans-4-(4-n-propylphenyl)cyclohexyl)ethyl)benzaldehyde 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 200 ml of heptane was added. Precipitate thus separated was filtered off, and subjected to a column chromatography over a silica gel by using ethyl acetate/heptane (1/5) as an eluent. Solvent was distilled off under a reduced pressure to obtain 5.6 g 4-(2-(4-(2-(trans-4-(4-n-propylphenyl)cyclohexyl)ethyl)phenyl)ethenyl)chlorobenzene.

Workup

  1. additionwas added to the suspension at room temperature
  2. stirringAfter stirred at room temperature for 2 hours
  3. extractionextracted with 300 ml of ethyl acetate
  4. washOrganic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under a reduced pressure
  7. addition200 ml of heptane was added
  8. customPrecipitate thus separated
  9. filtrationwas filtered off
  10. distillationSolvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-4e361b0acd8146c5bdcbf87512adb869
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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