Acetyl bromide → 1-Palmitoyl-2-linoleoyl-3-acetyl-rac-glycerol

HRID 252672Notes

Reaction equation

HRID 252672 reaction equation
[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]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 87183285HCID 87183285, compound

Product 1

HCID 99609251-Palmitoyl-2-linoleoyl-3-acetyl-rac-glycerolYield 28%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-aba5cbf79897441ba1922b1db8fc0ddd
Source dataset
uspto-grants-2011_01
Patent number
US07868196B2

Reaction notes

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