Tetrahydrofuran → HCID 178444476、化合物

HRID 1086779

反応式

HRID 1086779 の反応式
[H-].[Na+].O1CCCC1.[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[CH2:9][CH3:10].[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26](/[CH:29]=[CH:30]/[CH2:31]Br)[CH2:25][CH2:24]1)[CH2:19][CH2:20][CH2:21][CH3:22]>O>[CH2:18]([C@H:23]1[CH2:24][CH2:25][C@H:26](/[CH:29]=[CH:30]/[CH2:31][O:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13]2)[CH2:27][CH2:28]1)[CH2:19][CH2:20][CH2:21][CH3:22]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 178444431HCID 178444431、化合物HCID 178448131HCID 178448131、化合物

生成物 1

HCID 178444476HCID 178444476、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of 0.1 g of sodium hydride and 25 ml of tetrahydrofuran was treated with 0.5 g of trans-4-propylcyclohexanol while gassing with nitrogen, stirred for a further 2 hours, then treated with 1.0 g of (E)-3-(trans-4-pentylcyclohexyl)allyl bromide and subsequently heated to 70° C. overnight. Thereafter, the reaction mixture was treated with 500 ml of water and extracted four times with 50 ml of hexane each time. The combined organic phases were washed twice with 500 ml of water each time, dried over magnesium sulphate, filtered and then concentrated. The residue was purified by chromatography on silica gel with toluene. The trans-4-propylcyclohexyl (E)-3-(trans-4-pentylcyclohexyl)allyl ether obtained was recrystallized from acetone at -25° C.. This gave 1.2 g of pure product with m.p. (C-I) 26° C..

後処理

  1. extractionextracted four times with 50 ml of hexane each time
  2. washThe combined organic phases were washed twice with 500 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with toluene

出典と根拠

ORDレコード
ord-5c8405ed712a442bb4ec161ae8917048
出典データセット
uspto-grants-1991_07
特許番号
US05032312

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