Benzoin → HCID 15232721, 화합물

HRID 257618

반응식

HRID 257618 반응식
[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

참가 물질

9

반응물 4

HCID 8400BenzoinHCID 10868DicyclohexylcarbodiimideHCID 75009Monomethyl azelateHCID 517165Ammonium Acetate

생성물 1

HCID 15232721HCID 15232721, 화합물수율 78%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e7f1509404b4317bcfb630e66fb2d25
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262540

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