Potassium tert-butoxide → 1-[2-(4-Propylcyclohexyl)ethyl]-4-(4-vinylcyclohexyl)benzene

HRID 1893076노트

반응식

HRID 1893076 반응식
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][CH:27]([CH:30]=O)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][CH:27]([CH:30]=[CH2:1])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]

참가 물질

5

반응물 2

HCID 23665647Potassium tert-butoxideHCID 584532114-{4-[2-(4-Propyl-cyclohexyl)ethyl]phenyl}cyclohexane carbaldehyde

생성물 1

HCID 584532181-[2-(4-Propylcyclohexyl)ethyl]-4-(4-vinylcyclohexyl)benzene수율 80.1%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium tert-butoxide (0.86 g, 7.01 mmol) was added slowly with stirring for 3 minutes to 32 ml of solution including methyltriphenylphosphonium bromide (3 g, 8.41 mmol) dissolved in THF. Then, the solution was stirred for 30 minutes at a room temperature and THF solution (25 ml) of 4-{4-[2-(4-propyl-cyclohexyl)ethyl]phenyl}cyclohexane carbaldehyde (2.39 g, 7.01 mmol) was added slowly dropwise to reaction mixture, and then was stirred at a room temperature for 24 hours. The precipitate was filtered under reduced pressure and the filtrate was washed by water (100 ml) and extracted with ether (20 ml×1 time). The aqueous layer was extracted by chloroform (20 ml×3 times). The organic layer was collected, washed by NaCl solution, dried by anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36) and was recrystallized by addition of chloroform and ethanol to obtain 1.9 g (80%) of 1-[2-(4-propyl-cyclohexyl)ethyl]-4-(4-vinyl-cyclohexyl)benzene.

후처리

  1. stirringThen, the solution was stirred for 30 minutes at a room temperature
  2. stirringwas stirred at a room temperature for 24 hours
  3. filtrationThe precipitate was filtered under reduced pressure
  4. washthe filtrate was washed by water (100 ml)
  5. extractionextracted with ether (20 ml×1 time)
  6. extractionThe aqueous layer was extracted by chloroform (20 ml×3 times)
  7. customThe organic layer was collected
  8. washwashed by NaCl solution
  9. dry with materialdried by anhydrous Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36)
  12. customwas recrystallized by addition of chloroform and ethanol

출처 및 근거

ORD 기록
ord-06e3285655524a18910a0867f4598c00
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08512598B2

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