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

HRID 1665227

반응식

HRID 1665227 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e8e41aa57e314f299deb3938dbda5dc9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039500B2

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