Cyclohexanol → 6-Bromo-4-cyclohexyloxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 1077633

반응식

HRID 1077633 반응식
[Na].Br[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[C:6]([CH3:15])([CH3:14])[CH2:5][CH2:4]1.[CH:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[Br:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6]([CH3:15])([CH3:14])[CH2:5][CH2:4][CH:3]2[O:22][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

4

반응물 3

HCID 7966Cyclohexanol2회HCID 5360545Sodium2회HCID 196949614,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2회

생성물 1

HCID 196949636-Bromo-4-cyclohexyloxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

반응 조건

온도
70 °C

실험 절차

To 9 g (89.9 mmol) of cyclohexanol was added 160 mg (7.0 mmol) of sodium metal and the mixture was stirred at 70° C. for 12 hours. After all of the sodium dissolved the reaction mixture was cooled to ambient temperature and then a solution of 1 g (3.2 mmol) of 4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound I) in 1 ml of cyclohexanol was added. The mixture was heated at 120° C. for 4 hours and thereafter the excess solvent distilled off under reduced pressure. The product was dissolved in Et2O (75 ml), washed with water (5 ml) and brine (5 ml), dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (silica, 5% EtOAc-hexane) yielded the title compound as a colorless oil.

후처리

  1. temperaturewas cooled to ambient temperature
  2. temperatureThe mixture was heated at 120° C. for 4 hours
  3. distillationthe excess solvent distilled off under reduced pressure
  4. dissolutionThe product was dissolved in Et2O (75 ml)
  5. washwashed with water (5 ml) and brine (5 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography (silica, 5% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-ed805c429eba40b4820529c0471d9ca0
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05543534

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