Methyl 3-(bromomethyl)-2-benzofurancarboxylate → Methyl 3-dimethylaminomethylbenzofuran-2-carboxylate

HRID 29700

반응식

HRID 29700 반응식
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH2:10]Br)=[O:4].[CH3:16][NH:17][CH3:18].C1COCC1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH2:10][N:17]([CH3:18])[CH3:16])=[O:4]

참가 물질

5

반응물 2

HCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylateHCID 22320367Dimethylamine tetrahydrofuran

생성물 1

HCID 59710963Methyl 3-dimethylaminomethylbenzofuran-2-carboxylate수율 56.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-Bromomethylbenzofuran-2-carboxylic acid methyl ester (269 mg, 1 mmol) was dissolved in anhydrous DMF and added 2M dimethylamine/THF solution (1.5 ml, 3 mmol). After 1-2 h, the reaction was diluted with EtOAc and washed twice with saturated NaHCO3 (aq.) and brine. The organic extract over was dried over Na2SO4 and then concentrated in vacuo. The crude was purified on a silica gel column (5% MeOH in dichloromethane) to give 3-dimethylaminomethylbenzofuran-2-carboxylic acid methyl ester (131 mg).

후처리

  1. washwashed twice with saturated NaHCO3 (aq.) and brine
  2. extractionThe organic extract
  3. dry with materialover was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified on a silica gel column (5% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-b1416ea525ae4d63acecfe128d80009b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420089B2

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