Dibromomethane → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol

HRID 1074491노트

반응식

HRID 1074491 반응식
[Br:1][CH2:2][Br:3].[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=[CH:14][C:13]=1[CH:27]1[CH:32]([CH3:33])[CH:31]([CH3:34])[CH2:30][C:29](=[O:35])[CH2:28]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1([N-]C2CCCCC2)CCCCC1.[Li+]>O1CCCC1.O.CCOCC>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:25])([CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=[CH:14][C:13]=1[CH:27]1[CH:32]([CH3:33])[CH:31]([CH3:34])[CH2:30][C:29]([CH:2]([Br:3])[Br:1])([OH:35])[CH2:28]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 3

HCID 3024DibromomethaneHCID 10932176Lithium dicyclohexylamideHCID 204968423-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcyclohexanone

생성물 1

HCID 204969043-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a -78° C. solution of 17.4 g (0.10 mole) of dibromomethane and 21.7 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcyclohexanone in 100 ml of tetrahydrofuran is added dropwise over a period of 2 hours a solution of lithium dicyclohexylamide (0.10 mole) in 100 ml of tetrahydrofuran. The reaction is stirred one hour longer at -78° C. and quenched by addition of 2 ml (0.11 mole) of water. The reaction is added to 300 ml ether and 200 ml water. The ether extract is dried over magnesium sulfate and evaporated. The crude product is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to give pure 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol.

후처리

  1. extractionThe ether extract
  2. dry with materialis dried over magnesium sulfate
  3. customevaporated
  4. customThe crude product is purified via column chromatography on 500 g of silica gel
  5. washeluted with ether-pentane

출처 및 근거

ORD 기록
ord-8f70a67810b340bcb5be7b0f5b31fabf
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04391827

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