4'-Hydroxyacetophenone → 1-{4-[2-(4-Chlorophenyl)ethoxy]phenyl}ethanone

HRID 17739

반응식

HRID 17739 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.[CH:22]1[C:27]([CH2:28][CH2:29]O)=[CH:26][CH:25]=[C:24]([Cl:31])[CH:23]=1.CS(Cl)(=O)=O>CN(C=O)C>[Cl:31][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH2:29][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:22][CH:23]=1

참가 물질

7

반응물 5

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 74647p-Chlorophenethylic alcoholHCID 85257Methanesulfonate

생성물 1

HCID 669774911-{4-[2-(4-Chlorophenyl)ethoxy]phenyl}ethanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 4′-hydroxyacetophenone (4 mmol) in DMF (10 mL) at rt, solid potassium carbonate (12.0 mmol) was added. 4-chlorophenthoxy mesylate (prepared from the 4-chlorophenethanol and methanesulfonyl chloride) (4.4 mmol) was added to the reaction mixture and heated to 80° C. until completion according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was quenched with saturated sodium bicarbonate. The aqueous layer was poured into EtOAc (30 ml) and washed with water (2×15 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[2-(4-chlorophenyl)ethoxy]phenyl}ethanone. The crude alkylated product was purified by silica gel chromatography and the pure product obtained from 10% EtOAc/hexanes (yield 70%).

후처리

  1. additionwas added to the reaction mixture
  2. temperatureAfter cooling to rt
  3. customthe reaction mixture was quenched with saturated sodium bicarbonate
  4. additionThe aqueous layer was poured into EtOAc (30 ml)
  5. washwashed with water (2×15 ml) and brine (15 ml)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was removed in vacuuo

출처 및 근거

ORD 기록
ord-f910c620afc64b38affa936fd74b7d20
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737285B2

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