Carbon tetrabromide → 2,3-Dioleyloxypropyl azide

HRID 724757

반응식

HRID 724757 반응식
[CH2:1]([O:19][CH2:20][CH:21]([CH2:41]O)[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N-:43]=[N+:44]=[N-:45].[Li+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>CN(C)C=O>[CH2:23]([O:22][CH:21]([CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:41][N:43]=[N+:44]=[N-:45])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

참가 물질

6

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol

생성물 1

HCID 867518532,3-Dioleyloxypropyl azide수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1.00 g (1.7 mmol) of 1,2-O-dioleylglycerol, 0.83 g (17 mmol) of lithium azide, 0.89 g (3.4 mmol) of triphenylphosphine, and 1.13 g (3.4 mmol) of carbon tetrabromide was added 10 ml of N,N-dimethylformamide in bolus and the mixture was stirred at ambient temperature for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was diluted with water and extracted with ether. The ether layer was washed with water, dried, and concentrated, and the residue was purified by column chromatography (silica gel/n-hexane-ethyl acetate) to provide 1.03 g (100%) of 2,3-dioleyloxypropyl azide as oil.

후처리

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was diluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography (silica gel/n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-bfca62dd0eeb4eeb90172f288e21daae
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705188

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