Water → 2-Chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide

HRID 1815667ノート

反応式

HRID 1815667 の反応式
[CH3:1][C:2]([CH3:17])([CH2:15][OH:16])[CH:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)[OH:4].C(N(CC)CC)C.[P:25](Cl)(Cl)([Cl:27])=[O:26].O>ClCCl>[Cl:27][P:25]1(=[O:26])[O:4][CH:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:17])([CH3:1])[CH2:15][O:16]1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 225011452,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol

生成物 1

HCID 225011462-Chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide収率 67.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
3 °C

実験手順

2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol (83.6 g, 0.363 mol) and triethylamine (103.0 g, 1.018 mol) were dissolved in dichloromethane (300 ml). Phosphorus oxychloride (55.4 g, 0.361 mol) dissolved in dichloromethane (80 ml) was added dropwise to the solution above under cooling (2 to 4° C.) and with stirring for 1.5 hr. The solution was stirred at the same temperature for 1 hr, and water (150 ml) was added thereto to partition. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml) and the mixture was stirred thoroughly and then ice-cooled for 1 hr. The upper layer containing a large amount of unreacted 1-naphthoaldehyde was removed by decantation and the under layer was concentrated to give the title compound as a black tar (76.1 g, yield 67.8%).

後処理

  1. additionwas added dropwise to the solution above
  2. stirringThe solution was stirred at the same temperature for 1 hr
  3. customto partition
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml)
  8. stirringthe mixture was stirred thoroughly
  9. temperatureice-cooled for 1 hr
  10. additionThe upper layer containing a large amount of unreacted 1-naphthoaldehyde
  11. customwas removed by decantation
  12. concentrationthe under layer was concentrated

出典と根拠

ORDレコード
ord-32b75239a85244d7a630b33c00021d9e
出典データセット
uspto-grants-2005_04
特許番号
US06878831B2

反応ノート

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