Benzoin → HCID 15232721、化合物

HRID 257618

反応式

HRID 257618 の反応式
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](O)=O.C1([N:37]=C=NC2CCCCC2)CCCCC1.C([O-])(=O)C.[NH4+]>CN(C)C1C=CN=CC=1.O.C(O)(=O)C.ClCCl>[C:11]1([C:9]2[N:37]=[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]([O:18][CH3:17])=[O:30])[O:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

9

反応物 4

HCID 8400BenzoinHCID 10868DicyclohexylcarbodiimideHCID 75009Monomethyl azelateHCID 517165Ammonium Acetate

生成物 1

HCID 15232721HCID 15232721、化合物収率 78%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of benzoin (6.00 g, 28 mmol), azelaic acid monomethyl ester (7.17 g of 92% pure material, 32 mmol), 1,3-dicyclohexylcarbodiimide (7.00 g, 34 mmol), 4-dimethylaminopyridine (catalytic amount) and dichloromethane (120 mL) was stirred at room temperature. After 16 hours, the mixture was filtered and the solvent evaporated. Ammonium acetate (10.90 g, 141 mmol) and acetic acid (150 mL) were added to the residue and the mixture heated at reflux for 65 minutes before being cooled and diluted with water. The mixture was extracted with diethyl ether, the combined extracts dried over sodium sulfate and concentrated in vacuo. The residual oil was chromatographed on a column of silica gel using a mixture of hexanes and diethyl ether (7:3) as eluent to give methyl 4,5-diphenyl-2-oxazoleoctanoate (8.24 g, 77%) as an oil.

後処理

  1. filtrationthe mixture was filtered
  2. customthe solvent evaporated
  3. temperaturethe mixture heated
  4. temperatureat reflux for 65 minutes
  5. temperaturebefore being cooled
  6. extractionThe mixture was extracted with diethyl ether
  7. dry with materialthe combined extracts dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residual oil was chromatographed on a column of silica gel using
  10. additiona mixture of hexanes and diethyl ether (7:3) as eluent

出典と根拠

ORDレコード
ord-1e7f1509404b4317bcfb630e66fb2d25
出典データセット
uspto-grants-1993_11
特許番号
US05262540

関連ノート

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