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

HRID 252671
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HRID 252671 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 149001-MonopalmitinHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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)}.

후처리

  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

출처 및 근거

ORD 기록
ord-20a7c72a83ef44bbb45614e8e4beb78a
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07868196B2

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