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

HRID 899725

反応式

HRID 899725 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazole収率 55%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6344Dichloromethane溶媒

実験手順

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);

後処理

  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)

出典と根拠

ORDレコード
ord-40e01aa2676d487885ab6b6e19e01a73
出典データセット
uspto-grants-2008_04
特許番号
US07354934B2

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