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

HRID 626243

反応式

HRID 626243 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1a559c9705084fb5ba1aa4491ffb4216
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

関連ノート

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