1-(2-Trimethylsilylethoxymethyl)-2-hydroxymethylbenzimidazole → 1-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole

HRID 899580

반응식

HRID 899580 반응식
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][OH:17]>C(Cl)Cl.O=[Mn]=O>[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=[O:17]

참가 물질

4

반응물 1

HCID 226099341-(2-Trimethylsilylethoxymethyl)-2-hydroxymethylbenzimidazole

생성물 1

HCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole수율 55%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of the alcohol from above (26.58 g, 0.096 mol) in dry CH2Cl2 (450 mL) was added activated MnO2 (<5 micron, ˜85%, 93 g, 0.91 mol) and the suspension stirred at room temperature overnight. The mixture was filtered through celite© (175 g) and the cake was washed with CH2Cl2. The solvent was removed from the eluent under reduced pressure and the resultant residue purified by column chromatography on silica gel (3% MeOH/CH2Cl2) to provide the title aldehyde (14.41 g, 55%) as a pale yellow oil. 1H NMR (CDCl3) δ −0.07 (s, 9H), 0.90 (t, 2H, J=9 Hz), 3.56 (t, 2H, J=9 Hz), 6.04 (s, 2H), 7.43-7.51 (m, 2H), 7.66 (d, 1H, J=9 Hz), 7.95 (d, 1H, J=9 Hz), 10.13 (s, 1H); 13C NMR (CD3OD) δ −1.19, 17.94, 66.62, 73.30, 112.22, 122.51, 124.64, 127.43, 136.62, 143.11, 146.39, 185.10; ES-MS m/z (M+H);

후처리

  1. filtrationThe mixture was filtered through celite© (175 g)
  2. washthe cake was washed with CH2Cl2
  3. customThe solvent was removed from the eluent under reduced pressure
  4. customthe resultant residue purified by column chromatography on silica gel (3% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-367da760d312407ba5583480ffe7d17f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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