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

HRID 1660071ノート

反応式

HRID 1660071 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c853a3d34d454efcba4ac3d4605f625f
出典データセット
uspto-grants-1981_12
特許番号
US04306097

反応ノート

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