Allyl bromide → HCID 178459151、化合物

HRID 1029343ノート

反応式

HRID 1029343 の反応式
[H-].[Na+].[CH3:3][O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.[CH2:20](Br)[CH:21]=[CH2:22]>O1CCCC1>[CH2:20]([O:19][CH2:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:5][O:4][CH3:3])[CH2:7][CH2:8]2)[CH2:17][CH2:16]1)[CH:21]=[CH2:22]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178495625HCID 178495625、化合物

生成物 1

HCID 178459151HCID 178459151、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

150 mg of sodium hydride (as a 50 percent suspension in oil) is suspended in 10 ml of absolute tetrahydrofuran and then treated dropwise at room temperature within 3 minutes with a solution of 0.5 g of [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methanol in 8 ml of absolute tetrahydrofuran. The mixture is stirred for a further 5 minutes, then treated with 0.755 g of allyl bromide and stirred under reflux (bath temperature 70° C.) for 16 hours. Thereafter, the reaction mixture is partitioned in diethyl ether/water and extracted three times with diethyl ether. The organic phases are washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methyl allyl ether.

後処理

  1. stirringstirred
  2. customThereafter, the reaction mixture is partitioned in diethyl ether/water
  3. extractionextracted three times with diethyl ether
  4. washThe organic phases are washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

出典と根拠

ORDレコード
ord-eecfe7d4e7054e1389329de96d52bd07
出典データセット
uspto-grants-1992_04
特許番号
US05102578

反応ノート

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