1-Bromohexadecane → HCID 14350902、化合物

HRID 263833

反応式

HRID 263833 の反応式
[H-].[Na+].[C:3]([O:22][CH2:23][CH:24]([CH2:26][OH:27])[OH:25])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>CN(C)C=O>[CH2:29]([O:27][CH2:26][CH:24]([CH2:23][O:22][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[O:25][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

参加物

5

反応物 3

HCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 28828273-Trityloxypropane-1,2-diol

生成物 1

HCID 14350902HCID 14350902、化合物収率 68.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1H-nmr (200 MHz, CDCl3), 3.21 (2H, m), 3.65 (2H, m), 3.85 (1H, m), 7.4 (15H, m). ##STR17## Sodium hydride (prewashed with hexane, 60% oil dispersion, 0.79 g, 32.89 mmol) was stirred in dry dimethyl formamide (50 ml) under a stream of nitrogen. 1-trityl glycerol (5.0 g, 14.95 mmol) in dry dimethyl formamide (50 ml) was added carefully. The reaction was stirred at room temperature for 30 minutes before 1-bromohexadecane (9.13 g, 29.90 mmol) was added and the reaction was stirred at room temperature under a nitrogen atmosphere for 12 hours. The reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3). The organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml), dried over sodium sulphate and evaporated to yield the crude product, which was purified by column chromatography eluting with (40-60) light petroleum: ethyl acetate (230:20). Fractions containing product were evaporated to dryness to give 1,2-dihexadecyl-3-trityl glycerol (8.00 g, 10.21 mmol) 68% yield

後処理

  1. additionwas added
  2. customThe reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3)
  3. washThe organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto yield the crude product, which
  7. customwas purified by column chromatography
  8. washeluting with (40-60) light petroleum: ethyl acetate (230:20)
  9. additionFractions containing product
  10. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-01fff633c6774e4eb8c309ed33313eba
出典データセット
uspto-grants-1997_07
特許番号
US05645883

関連ノート

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