Potassium Iodide → 1,2-diphenylethanone O-(2-bromoethyl)oxime

HRID 975249

反応式

HRID 975249 の反応式
[C:1]1([C:7](=[N:15][OH:16])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[Br:17][CH2:18][CH2:19][O:16][N:15]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 2353831,2-Diphenyl-1-ethanone oxime

生成物 1

HCID 544627271,2-diphenylethanone O-(2-bromoethyl)oxime

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

A suspension of the above oxime (5.0 g, 24 mmol), 1,2-dibromoethane (25 ml) and potassium carbonate (10.0 g, 72 mmol) in acetone (25 ml) was heated at reflux for 1 h, then stirred at ambient temperature for 72 h and finally heated at reflux for 4.5 h. Potassium iodide (0.5 g) was added and refluxing continued for an additional 16 h. Water (100 ml) was added and the resulting mixture extracted with dichloromethane (2×100 ml). The combined organic phases were washed with water (100 ml) and brine (10 ml) and dried (MgSO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (60 g, n-heptane/ethyl acetate 10/1) to give 3.6 g of 1,2-diphenylethanone O-(2-bromoethyl)oxime.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperaturefinally heated
  4. temperatureat reflux for 4.5 h
  5. temperaturerefluxing
  6. waitcontinued for an additional 16 h
  7. extractionthe resulting mixture extracted with dichloromethane (2×100 ml)
  8. washThe combined organic phases were washed with water (100 ml) and brine (10 ml)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated in vacuo
  11. customthe residue was purified by column chromatography on silica gel (60 g, n-heptane/ethyl acetate 10/1)

出典と根拠

ORDレコード
ord-6fa59199fd4b47ce95560c8b2553ec22
出典データセット
uspto-grants-1997_03
特許番号
US05608069

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