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

HRID 1660072ノート

反応式

HRID 1660072 の反応式
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18]CCC)[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][C:26]([CH:33](Br)Br)([OH:32])[CH2:25]1)C1C=CC=CC=1.[CH2:36]([Li])[CH2:37][CH2:38][CH3:39]>O1CCCC1>[CH2:36]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:11][CH2:12][CH3:13])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][CH2:33][C:26](=[O:32])[CH2:25]1)[C:37]1[CH:14]=[CH:9][CH:10]=[CH:39][CH:38]=1

参加物

4

反応物 2

HCID 204969043-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanolHCID 178418339Butyllithium

生成物 1

HCID 204968973-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcycloheptanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a -78° C. solution of 30.4 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol in 150 ml of tetrahydrofuran is slowly added over a period of 2 hours 47.7 ml (0.105 mole) of n-butyllithium (2.2 M in hexane). The reaction solution is stirred 2 hours longer at -78° C. and 10 minutes at 0° C. and then quenched by pouring into 300 ml of ice cold 1 N hydrochloric acid. The quenched reaction is extracted with two 250 ml portions of ether, the combined extract washed with 250 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to yield the title compound.

後処理

  1. customquenched
  2. additionby pouring into 300 ml of ice cold 1 N hydrochloric acid
  3. customThe quenched reaction
  4. extractionis extracted with two 250 ml portions of ether
  5. extractionthe combined extract
  6. washwashed with 250 ml of saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue is purified via column chromatography on 500 g of silica gel
  10. washeluted with ether-pentane

出典と根拠

ORDレコード
ord-d2d0480ac9e1478db4a908690e041fb4
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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