Phenol → HCID 9909232, 화합물

HRID 1637200노트

반응식

HRID 1637200 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[O:7]([C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 11046271HCID 11046271, 화합물

생성물 1

HCID 9909232HCID 9909232, 화합물수율 17%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

Phenol (108 mg, 1.15 mmol) was added to a stirred suspension of sodium hydride (46 mg of 60% dispersion in mineral oil, 1.15 mmol) in anhydrous dimethylformamide (1 ml), under a nitrogen atmosphere. Ethyl 3-chloro-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Preparation 4, 200 mg, 0.58 mmol) was added to the mixture after 30 minutes, and the mixture was then heated to 75° C. for 48 hours. The reaction was partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using diethyl ether as eluant. The isolated product was crystallised from hexane to give the title compound as a colourless solid (40 mg).

후처리

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel
  7. customThe isolated product was crystallised from hexane

출처 및 근거

ORD 기록
ord-184108eb7b4e4b9dbc1139184ebfd988
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06040309

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