Sodium hydride → Methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate

HRID 2248904노트

반응식

HRID 2248904 반응식
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[H-].[Na+].[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Cl>CN(C=O)C>[CH3:13][O:12][C:10]([C:7]1[S:6][C:5]2[CH:14]=[CH:15][C:2]([O:1][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[C:30]([O:29][CH2:28][C:19]4[CH:20]=[CH:21][C:22]5[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:18]=4)[CH:31]=3)=[CH:3][C:4]=2[C:8]=1[CH3:9])=[O:11]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 19994682Methyl 5-hydroxy-3-methylbenzo(b)thiophene-2-carboxylate

생성물 1

HCID 54370568Methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of methyl 5-hydroxy-3-methyl-benzo(b)thiophene-2-carboxylate (878.6 mg, 3.96 mmol) in dry DMF (20 ml) at room temperature is added sodium hydride (158 mg, 3.95 mmol) as a 60% dispersion in mineral oil. After 30 minutes of stirring 3-(2-quinolinylmethoxy)benzyl chloride (1.02 g, 3.60 mmol) is added. The solution is stirred at room temperature for 4 hours and quenched with ice-water. Extraction with ethyl acetate, washing with aqueous sodium carbonate, water and brine is followed by drying (MgSO4) and concentration. The residue is subjected to flash chromatography on silica gel. Elution with 25% ether in hexane affords methyl-3-methyl-5-[3-(2-quinolinylmethoxy)benzyloxy]benzo(b) -thiophene-2-carboxylate.

후처리

  1. customquenched with ice-water
  2. extractionExtraction with ethyl acetate
  3. washwashing with aqueous sodium carbonate, water and brine
  4. customby drying
  5. concentration(MgSO4) and concentration
  6. washElution with 25% ether in hexane

출처 및 근거

ORD 기록
ord-c0e7d9106c634bb68877df1a6a62d236
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05041453

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