Methane, dichloromethoxy- → HCID 178418754、化合物

HRID 10729

反応式

HRID 10729 の反応式
[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=3[O:17][CH3:18])[N:8]=2)[CH2:3][CH2:2]1.[CH3:19][O:20]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[C:10]([O:17][CH3:18])=[CH:11][C:12]([O:15][CH3:16])=[C:13]([CH:14]=3)[CH:19]=[O:20])[N:8]=2)[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 21004Methane, dichloromethoxy-HCID 178418803HCID 178418803、化合物

生成物 1

HCID 178418754HCID 178418754、化合物

試薬・触媒・溶媒 1

HCID 24193Titanium Tetrachloride触媒

実験手順

Ex-105B: To a solution of 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole (0.51 g, 2.09 mmol) was added dichloromethyl methyl ether (0.28 mL, 3.13 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 8.4 mL, 8.4 mmol) dropwise at 0° C. The solution was allowed to warm up to ambient temperature and stir for 4.5 hours. The reaction mixture was then poured into ice. The aqueous layer was adjusted to pH 12 and extracted with dichloromethane. The combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine, dried over sodium sulfate and concentrated to afford 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde which was used without further purification. 1H NMR (DMSO-d6) δ 13.95 (bs, 1H), 10.22 (s, 1H), 8.09 (s, 1H), 7.70 (s, 1H), 6.88 (s, 1H), 4.04 (s, 3H), 4.00 (s, 3H), 2.25 (m, 1H), 1.20 (m, 4H). MS m/z=245 ([M+H]+, 100%).

後処理

  1. additionThe reaction mixture was then poured into ice
  2. extractionextracted with dichloromethane
  3. washThe combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-fcfe69e46057466bbea048d283df22b7
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

関連ノート

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