Imidazole → 1-Palmitoyl-3-t-butyldimethylsilyl-glycerol

HRID 252671Notes

Reaction equation

HRID 252671 reaction equation
[C:1]([O:18][CH2:19][CH:20]([CH2:22][OH:23])[OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].N1C=CN=C1.[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>ClCCl>[C:1]([O:18][CH2:19][CH:20]([CH2:22][O:23][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 149001-MonopalmitinHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 853956141-Palmitoyl-3-t-butyldimethylsilyl-glycerolYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-palmitoyl-glycerol (33.0 g), dichloromethane (330 ml) and imidazole (13.6 g) were added into 1 L reactor, and the reaction mixture was cooled to 0° C. Then, t-butyl-dimethylsilylchloride (18.0 g) was added, and the reaction mixture was stirred for 2 hours. After filtering the reaction mixture, the solvent was removed by distillation under reduced pressure, and purified water (165 ml) and heptane (150 ml) were added for an extraction. The separated organic layer was extracted with purified water (80 ml) again, and then the organic layer was dehydrated with anhydrous MgSO4, and filtered. Then, the solvent was removed by distillation under reduced pressure to obtain 1-palmitoyl-3-t-butyldimethylsilyl-glycerol (yield: 100%) {1H NMR (400 MHz, CDCl3): δ 0.78-0.83 (m, 18H), 1.18-1.31 (m, 24H), 1.50-1.56 (m, 2H), 2.24 (t, 2H), 3.51-3.60 (m, 2H), 3.76-3.79 (p, 1H), 4.01-4.10 (m, 2H)}.

Workup

  1. filtrationAfter filtering the reaction mixture
  2. customthe solvent was removed by distillation under reduced pressure
  3. custompurified water (165 ml) and heptane (150 ml)
  4. additionwere added for an extraction
  5. extractionThe separated organic layer was extracted with purified water (80 ml) again
  6. filtrationfiltered
  7. customThen, the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-20a7c72a83ef44bbb45614e8e4beb78a
Source dataset
uspto-grants-2011_01
Patent number
US07868196B2

Reaction notes

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