Acetic Acid → (R)-4-Bromostyrene oxide

HRID 2114445ノート

反応式

HRID 2114445 の反応式
C(O)(=O)C.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:14][O:13]2)=[CH:8][CH:7]=1.O>C1(C)C=CC=CC=1.C1COCC1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[CH2:14][O:13]2)=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 1194602-(4-Bromophenyl)oxirane

生成物 1

HCID 11217859(R)-4-Bromostyrene oxide収率 82%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a magnetically stirred solution of (R,R)-(−)-N,N′-Bis(3,5-di-tert-butyl-salicylidene-1,2-cyclohexane-diaminocobalt(II) (4.88 g, 8.09 mmol) in toluene (50 mL) at room temperature in an open flask, was added acetic acid (4.6 mL, 80.0 mmol). The mixture was stirred for 1 h. The mixture was then concentrated to give a brown solid, which was placed under high vacuum overnight. The brown residue was taken up in THF (50 mL) and the resulting solution was added to 2-(4-bromophenyl)oxirane (199.62 g, 1.0 mol) in THF (150 mL). The reaction mixture was cooled to 0° C. and distilled water (10.0 mL, 556 mmol) was added dropwise over 5 minutes into the mixture. The resulting mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was concentrated and then 5% EtOAc/Hexane (500 mL) was added to the residue. The insoluble material was filtered off. The filtrate was concentrated and the resulting brown oil was diluted with hexane (500 mL). The insoluble material was removed by filtration and the filtrate was concentrated to give a brown oil. The crude material was purified by vacuum distillation at 90° C. to give (2R)-2-(4-bromophenyl)oxirane as a clear oil (72.7 g, 365 mmol, 82%) which solidified upon cooling to a white solid.

後処理

  1. concentrationThe mixture was then concentrated
  2. customto give a brown solid, which
  3. customwas placed under high vacuum overnight
  4. additionwas added dropwise over 5 minutes into the mixture
  5. temperatureThe resulting mixture was warmed to room temperature
  6. stirringstirred for 18 h
  7. concentrationThe reaction mixture was concentrated
  8. addition5% EtOAc/Hexane (500 mL) was added to the residue
  9. filtrationThe insoluble material was filtered off
  10. concentrationThe filtrate was concentrated
  11. additionthe resulting brown oil was diluted with hexane (500 mL)
  12. customThe insoluble material was removed by filtration
  13. concentrationthe filtrate was concentrated
  14. customto give a brown oil
  15. distillationThe crude material was purified by vacuum distillation at 90° C.

出典と根拠

ORDレコード
ord-9b6ceaa592cc49ae80cacbb23d70a019
出典データセット
uspto-grants-2008_10
特許番号
US07432258B2

反応ノート

読み込み中…