Sodium hydride → 5-Benzyl-1-benzyloxymethyl-4-isopropyl-2-methyl-1H-imidazole

HRID 2259241

反応式

HRID 2259241 の反応式
[CH2:1]([C:8]1[NH:12][C:11]([CH3:13])=[N:10][C:9]=1[CH:14]([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]([O:26][CH2:27]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([C:8]1[N:12]([CH2:27][O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]([CH3:13])=[N:10][C:9]=1[CH:14]([CH3:16])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 190029815-Benzyl-4-isopropyl-2-methylimidazole

生成物 1

HCID 4758905-Benzyl-1-benzyloxymethyl-4-isopropyl-2-methyl-1H-imidazole収率 53.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 980 mg of 5-benzyl-4-isopropyl-2-methylimidazole (4.58 mmol) in 9.8 ml of dry dimethylformamide is added 238 mg of 60% oil suspension of sodium hydride (5.95 mmol) under ice cooling. Ten minutes later, 935 mg of benzyloxymethyl chloride (5.97 mmol) is dropwise added. One hour later, the reaction mixture is poured onto ice water and extracted with ethyl acetate. The extract is washed with saturated brine, dried over sodium sulfate, filtered and the filtrate is concentrated in vacuo. The crude product is chromatographed on a column of silica gel, eluting with ethyl acetate and n-hexane (1:1) to give 820 mg of the objective 5-benzyl-1-benzyloxymethyl-4-isopropyl-2-methylimidazole (I-42). Yield, 54.17%.

後処理

  1. additionOne hour later, the reaction mixture is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe crude product is chromatographed on a column of silica gel
  8. washeluting with ethyl acetate and n-hexane (1:1)

出典と根拠

ORDレコード
ord-2385914973c64281946fbd13d428a7bf
出典データセット
uspto-grants-1995_12
特許番号
US05472965

関連ノート

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