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

HRID 975249

반응식

HRID 975249 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6fa59199fd4b47ce95560c8b2553ec22
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05608069

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