Ammonium Chloride → 3-[2-(Mesitylmethyl)-1-methyl-1H-benzimidazol-7-yl]pentan-3-ol

HRID 1665227

反応式

HRID 1665227 の反応式
[C:1]1([CH3:24])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([C:20](OC)=[O:21])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1.[CH2:25]([Li])[CH3:26].[CH:28]1C=CC=C[CH:29]=1.C1CCCCC1.[Cl-].[NH4+]>O1CCCC1>[C:1]1([CH3:24])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([C:20]([OH:21])([CH2:25][CH3:26])[CH2:28][CH3:29])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 18624872Benzene--cyclohexane (1/1)HCID 59202086Methyl 2-(mesitylmethyl)-1-methyl-1H-benzimidazole-7-carboxylateHCID 178506846HCID 178506846、化合物

生成物 1

HCID 249864303-[2-(Mesitylmethyl)-1-methyl-1H-benzimidazol-7-yl]pentan-3-ol収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-(mesitylmethyl)-1-methyl-1H-benzimidazole-7-carboxylate (1.30 g, 4.0 mmol) in tetrahydrofuran (80 mL) was added a solution of ethyllithium in benzene/cyclohexane (90/10) (0.5 M, 32 mL, 16.1 mmol) dropwise at −78° C. The solution was warmed to room temperature over 1 hr followed by addition of saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (100 mL, three times) and the combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 15-25% ethyl acetate/n-hexane gradient mixture to give the title compound (590 mg, 1.68 mmol, 42%) as a colorless solid. The resulting solid was recrystallized from n-hexane/ethyl acetate to give the title compound (435 mg, 1.24 mmol).

後処理

  1. extractionThe mixture was extracted with ethyl acetate (100 mL, three times)
  2. washthe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 15-25% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-e8e41aa57e314f299deb3938dbda5dc9
出典データセット
uspto-grants-2011_10
特許番号
US08039500B2

関連ノート

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