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

HRID 2248904ノート

反応式

HRID 2248904 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0e7d9106c634bb68877df1a6a62d236
出典データセット
uspto-grants-1991_08
特許番号
US05041453

反応ノート

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