Acetic Acid → 7-(1-Ethylpropyl)-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

HRID 1665229ノート

反応式

HRID 1665229 の反応式
[CH2:1]([C:3]([C:6]1[C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])=[N:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH:4][CH3:5])[CH3:2].C(O)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=3[CH3:22])=[N:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 674389407-[1-Ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

生成物 1

HCID 249864327-(1-Ethylpropyl)-2-(mesitylmethyl)-1-methyl-1H-benzimidazole収率 11%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 7-[1-ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole (110 mg, 0.331 mmol) in tetrahydrofuran (3.5 mL) was added a solution of borane-dimethyl sulfide complex in tetrahydrofuran (1.9 M, 3.5 mL, 6.63 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 15 hr, acetic acid (5.0 mL) was added to the mixture and the mixture was heated at 120° C. for 2 hr. After the reaction mixture was cooled, the mixture was poured into saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL, twice). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 10-25% ethyl acetate/n-hexane gradient mixture to give the title compound (12 mg, 0.0359 mmol, 11%) as a colorless solid.

後処理

  1. temperaturethe mixture was heated at 120° C. for 2 hr
  2. temperatureAfter the reaction mixture was cooled
  3. extractionextracted with ethyl acetate (50 mL
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 10-25% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-e3b674f2f3d544e599ea4fdf39515489
出典データセット
uspto-grants-2011_10
特許番号
US08039500B2

反応ノート

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