2-Chloromethylbenzimidazole → 2-Chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole

HRID 7130

반응식

HRID 7130 반응식
[Cl:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>C1COCC1>[Cl:1][CH2:2][C:3]1[N:4]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 785712-ChloromethylbenzimidazoleHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

생성물 1

HCID 220187062-Chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole수율 67.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-chloromethylbenzimidazole (1.89 g, 11.4 mmol) in dry THF (57 mL) was added N,N-diisopropylethylamine (3.00 mL, 17.2 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (1.90 mL, 10.8 mmol) both via syringe under nitrogen at room temperature. The mixture was stirred for 3 days at which time the solvent was removed in vacuo. The residue was taken up in CH2Cl2 (100 mL) and washed with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. Purification by flash chromatography (silica gel, 100:2:1 CH2Cl2-methanol-ammonium hydroxide) provided 2.17 g (65%) of the title compound as a yellow oil, which solidified on standing. 1H NMR (CDCl3) δ−0.06 (s, 9H), 0.92 (t, 2H, J=7.5 Hz), 3.57 (t, 2H, J=7.5 Hz), 4.91 (s, 2H), 5.65 (s, 2H), 7.31–7.36 (m, 2H), 7.50 (d, 1H, J=7.5 Hz), 7.78 (d, 1H, J=7.5 Hz).

후처리

  1. customwas removed in vacuo
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product as a yellow oil
  7. customPurification by flash chromatography (silica gel, 100:2:1 CH2Cl2-methanol-ammonium hydroxide)

출처 및 근거

ORD 기록
ord-da10064715ba4368ab44a1416b1d9cee
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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