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

HRID 252672노트

반응식

HRID 252672 반응식
[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]

참가 물질

4

반응물 2

HCID 10482Acetyl bromideHCID 87183285HCID 87183285, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8900Heptane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-aba5cbf79897441ba1922b1db8fc0ddd
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868196B2

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