Allyl bromide → 1,2-di-O-(n-hexadecyl)-3-allyl-glycerol

HRID 1701595

反応式

HRID 1701595 の反応式
[H-].[Na+].[CH2:3]([O:19][CH2:20][CH:21]([CH2:39][OH:40])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:41](Br)[CH:42]=[CH2:43]>CN(C)C=O.O>[CH2:3]([O:19][CH2:20][CH:21]([CH2:39][O:40][CH2:43][CH:42]=[CH2:41])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 1025482,3-Bis(hexadecyloxy)propan-1-ol

生成物 1

HCID 234661031,2-di-O-(n-hexadecyl)-3-allyl-glycerol収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Sodium hydride (1.78 g. of 50 wt. % dispersion in mineral oil, 37 mmoles) was added at 60° C. to a solution of 1,2-di-O-(n-hexadecyl)-glycerol (10 g., 18.5 mmoles) in N,N-dimethylformamide (100 ml.), and the resulting solution stirred for 20 minutes at 60° C. Allyl bromide (4.47 g., 37 mmoles) was then added dropwise and the resulting mixture stirred for 3 hours at 90° C., cooled, cautiosly diluted with water (200 ml.) to quench the reaction, and extracted with ether (3×150 ml.). The combined ether extract was washed with saturated aqueous sodium chloride solution, dried (MgSO4), filtered and evaporated in vacuo to an oil, which was purified by silica gel chromatography (elution with benzene) [10 g., 93% yield, oil, n.m.r. (CDCl3) δ 5.66-6.16 (m, 1, --OCH2CH=CH2), 5.25 (d of doublets, 2, --OCH2CH=CH2) and 4.03 (d, 2, --OCH2CH=CH2)].

後処理

  1. stirringthe resulting mixture stirred for 3 hours at 90° C.
  2. temperaturecooled
  3. customto quench
  4. customthe reaction
  5. extractionextracted with ether (3×150 ml.)
  6. extractionThe combined ether extract
  7. washwas washed with saturated aqueous sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo to an oil, which
  11. customwas purified by silica gel chromatography (elution with benzene) [10 g., 93% yield, oil, n.m.r. (CDCl3) δ 5.66-6.16 (m, 1, --OCH2CH=CH2), 5.25 (d of doublets, 2, --OCH2CH=CH2) and 4.03 (d, 2, --OCH2CH=CH2)]

出典と根拠

ORDレコード
ord-ab42812d146c4f84a092492634ec97f7
出典データセット
uspto-grants-1980_03
特許番号
US04193999

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