Acetyl bromide → 9,12-Octadecadienoic acid (9Z,12Z)-, 1-((acetyloxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl ester

HRID 252672ノート

反応式

HRID 252672 の反応式
[C:1](Br)(=[O:3])[CH3:2].[C:5]([O:22][CH2:23][CH:24]([CH2:45][O:46][Si](C(C)(C)C)(C)C)[O:25][C:26](=[O:44])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CCCCCCC>[C:5]([O:22][CH2:23][CH:24]([CH2:45][O:46][C:1](=[O:3])[CH3:2])[O:25][C:26](=[O:44])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

4

反応物 2

HCID 10482Acetyl bromideHCID 87183285HCID 87183285、化合物

生成物 1

HCID 99609259,12-Octadecadienoic acid (9Z,12Z)-, 1-((acetyloxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl ester収率 28%

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒2 回

実験手順

Acetylbromide (123 g) was added into heptane solution of 1-palmitoyl-2-linoleoyl-3-t-butyl-dimethylsilyl-glycerol, which was obtained in Example 4, and the reaction mixture was stirred for 12 hours at room temperature. Heptane (400 ml) was added into the reaction mixture, and the cooling purified water (400 ml) was dropwisely added thereto for extracting the organic layer. The separated organic layer was washed with a solution of saturated sodium bicarbonate (100 ml) and purified water (400 ml), and then the washed organic layer was dehydrated with anhydrous MgSO4, and filtered. 1-palmitoyl-2-linoleoyl-3-acetyl-glycerol (178 g) was obtained with a silica gel (Si-60, 230-400 mesh) column chromatography(heptane:ethyl acetate=36:1 by volume) (theoretical amounts: 63.5 g, yield: 28.0%).

後処理

  1. customwhich was obtained in Example 4
  2. customthe cooling purified water (400 ml)
  3. additionwas dropwisely added
  4. extractionfor extracting the organic layer
  5. washThe separated organic layer was washed with a solution of saturated sodium bicarbonate (100 ml)
  6. custompurified water (400 ml)
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-aba5cbf79897441ba1922b1db8fc0ddd
出典データセット
uspto-grants-2011_01
特許番号
US07868196B2

反応ノート

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