p-Toluenesulfonic acid → (2S)-2-(4,5-diphenyloxazol-2-yl)oxirane

HRID 380122ノート

反応式

HRID 380122 の反応式
[OH:1][C@H:2]([C:5]1[O:6][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:9]=1)[CH2:3]O.COC(OC)(OC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:10]1([C:8]2[N:9]=[C:5]([C@@H:2]3[CH2:3][O:1]3)[O:6][C:7]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 15050Trimethyl orthoacetateHCID 569827262-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole

生成物 1

HCID 57131304(2S)-2-(4,5-diphenyloxazol-2-yl)oxirane収率 75.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole (20 g) in CH2Cl2 (400 ml) were added orthoacetic acid trimethyl ester (12.8 ml) and p-toluenesulfonic acid (130 mg) at room temperature under N2. After being stirred for 30 minutes, the solvent was evaporated in vacuo. The residue was diluted with CH2Cl2 (200 ml) and acetyl bromide (7.6 ml) was added to the solution at 0° C. under N2. After being stirred for 2 hours at room temperature, the solvent was evaporated in vacuo, the residue was diluted with methanol (200 ml), and K2CO3 (16 g) was added to the solution at 0° C. The mixture was stirred for 30 minutes at the same temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by trituration with ether-hexane to give (2S)-2-(4,5-diphenyloxazol-2-yl)oxirane (14.2 g).

後処理

  1. customthe solvent was evaporated in vacuo
  2. additionThe residue was diluted with CH2Cl2 (200 ml) and acetyl bromide (7.6 ml)
  3. additionwas added to the solution at 0° C. under N2
  4. stirringAfter being stirred for 2 hours at room temperature
  5. customthe solvent was evaporated in vacuo
  6. additionthe residue was diluted with methanol (200 ml), and K2CO3 (16 g)
  7. additionwas added to the solution at 0° C
  8. stirringThe mixture was stirred for 30 minutes at the same temperature
  9. custompartitioned between ethyl acetate and water
  10. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  11. customThe dried solvent was evaporated in vacuo
  12. customthe residue was purified by trituration with ether-hexane

出典と根拠

ORDレコード
ord-cb4b9426a9eb4fbb809235ba54cd9bdd
出典データセット
uspto-grants-2001_10
特許番号
US06300344B1

反応ノート

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