Water → 1,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol

HRID 444063

反応式

HRID 444063 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].[C:41]([C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][CH:50]=1)[CH2:46]Br)#[N:42].O>O1CCCC1>[CH2:3]([O:19][CH2:20][CH:21]([CH2:39][O:40][CH2:46][C:45]1[CH:48]=[CH:49][CH:50]=[C:43]([C:41]#[N:42])[CH:44]=1)[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 4

HCID 962WaterHCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 1025482,3-Bis(hexadecyloxy)propan-1-ol

生成物 1

HCID 234661581,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (1.056 g. of 50 wt. % mineral oil dispersion, 22 mmoles) was added to a solution of 1,2-di-O-(n-hexadecyl)-glycerol (9.73 g., 18 mmoles) in tetrahydrofuran (150 ml.) and the resulting solution stirred for 20 minutes at room temperature under nitrogen. m-Cyanobenzyl bromide (4.0 g., 20 mmoles) was added and the reaction mixture stirred overnight at room temperature under nitrogen. Water (200 ml.) was then added cautiously and the resulting mixture extracted with ethyl acetate (3×150 ml.). The combined ethyl acetate extract was dried (MgSO4), filtered and evaporated in vacuo to an oil (12 g.), which was purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ].

後処理

  1. stirringthe reaction mixture stirred overnight at room temperature under nitrogen
  2. extractionthe resulting mixture extracted with ethyl acetate (3×150 ml.)
  3. extractionThe combined ethyl acetate extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil (12 g.), which
  7. customwas purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ]

出典と根拠

ORDレコード
ord-d0d52e488d75449eaa6c34ec73bff122
出典データセット
uspto-grants-1981_04
特許番号
US04262021

関連ノート

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