Tetrahydrofuran → 1-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-one

HRID 626243

반응식

HRID 626243 반응식
CON(C)[C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]([CH3:13])[CH:11]=[N:12][C:8]=2[CH:7]=1)=[O:5].[CH2:17]1COC[CH2:18]1>>[CH3:13][N:10]1[C:9]2[CH:14]=[CH:15][C:6]([C:4](=[O:5])[CH2:17][CH3:18])=[CH:7][C:8]=2[N:12]=[CH:11]1

참가 물질

3

반응물 2

HCID 8028TetrahydrofuranHCID 86665700N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide

생성물 1

HCID 391039641-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-one수율 94%

실험 절차

To a solution of N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide (900 mg, 1.0 eq) in 30 mL anhydrous THF was added 3 M EtBrMg (9 mL, 6.0 eq) slowly at 0° C. The reaction was stirred at rt overnight, quenched with sat NH4Cl (aq), and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (730 mg, 94%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.04 (J=8.4 Hz, 1.6 Hz, 1H), 7.95 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 3.10 (q, J=7.2 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H).

후처리

  1. customquenched with sat NH4Cl (aq)
  2. extractionextracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-1a559c9705084fb5ba1aa4491ffb4216
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

연결된 노트

불러오는 중…