Hydrochloric Acid → Carbonic acid 4-nitro-phenyl ester (R)-1-phenyl-ethyl ester

HRID 450015

反応式

HRID 450015 の反応式
[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.CC1CCCO1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24].Cl>O>[C:1]1([C@H:7]([O:9][C:23](=[O:24])[O:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73012-MethyltetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 6375161-Phenylethanol, (R)-

生成物 1

HCID 11108942Carbonic acid 4-nitro-phenyl ester (R)-1-phenyl-ethyl ester収率 98.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of (R)-1-phenyl-ethanol (60.6 g, 0.496 mol), pyridine (42.5 mL, 0.526 mol) and 2-methyl-tetrahydrofuran (600 mL) was cooled to 0° C. and p-nitrophenyl chloroformate (100 g, 0.496 mol) was added over 15 min keeping the internal temperature below 5° C. The reaction mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added 1.0 M HCl in water (300 mL). Layers were separated. The organic layer was washed with 1N HCl (300 mL) and brine (300 mL), filtered, concentrated to dryness by rotary evaporation, and dried under vacuum to give the title compound (140 g) as a clear yellow oil.

後処理

  1. customthe internal temperature below 5° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customLayers were separated
  4. washThe organic layer was washed with 1N HCl (300 mL) and brine (300 mL)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-a568c78deb4940e9896e3763c7216612
出典データセット
uspto-grants-2013_07
特許番号
US08486958B2

関連ノート

読み込み中…