Carbon tetrabromide → 2,3-Dioleyloxypropyl azide

HRID 724757

反応式

HRID 724757 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 867518532,3-Dioleyloxypropyl azide収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bfca62dd0eeb4eeb90172f288e21daae
出典データセット
uspto-grants-1998_01
特許番号
US05705188

関連ノート

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