Acetaldehyde → HCID 68762714、化合物

HRID 1628578ノート

反応式

HRID 1628578 の反応式
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][OH:23])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:24](=O)[CH3:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][OH:23])[C:7]2[C:2]([N:1]([CH2:24][CH3:25])[CH2:27][CH3:28])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

参加物

8

反応物 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68762744HCID 68762744、化合物

生成物 1

HCID 68762714HCID 68762714、化合物収率 99.1%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 2-{7-amino-2-[(2,4-dichlorophenyl) (hydroxy)methyl]-1H-benzimidazol-1-yl}ethanol (7.58 g, 21.5 mmol) in methanol (220 mL) and acetic acid (11 mL) was added acetoaldehyde (8.04 mL, 129 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (27.3 g, 129 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 2 h, the mixture was diluted with aqueous sodium hydrogen carbonate and water, and extracted with ethyl acetate. The combined organic layer was washed with 1N aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford a crude solid, which was washed with diisopropylether to give the title compound as a colorless solid (8.70 g, 21.3 mmol, 99%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 1N aqueous sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  7. customto afford a crude solid, which
  8. washwas washed with diisopropylether

出典と根拠

ORDレコード
ord-173a46d370504371acc4dd2811dd34a3
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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