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

HRID 1215

反応式

HRID 1215 の反応式
[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

参加物

4

反応物 3

HCID 7966Cyclohexanol2 回HCID 5360545Sodium2 回HCID 196949614,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2 回

生成物 1

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

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9d51c679b094d58b2ae53013e4113f3
出典データセット
uspto-grants-1998_03
特許番号
US05723620

関連ノート

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