Hantzsch ester → 3-Hydroxy-2-(3-(2-((triisopropylsilyl)oxy)ethyl)benzyl)cyclopent-2-enone

HRID 41146

반응식

HRID 41146 반응식
[CH:1]([Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)([CH3:3])[CH3:2].[CH2:22]1[C:27](=[O:28])[CH2:26][C:24](=[O:25])[CH2:23]1.N1CCC[C@H]1C(O)=O.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>ClCCl>[OH:25][C:24]1[CH2:23][CH2:22][C:27](=[O:28])[C:26]=1[CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([CH2:7][CH2:6][O:5][Si:4]([CH:19]([CH3:21])[CH3:20])([CH:1]([CH3:3])[CH3:2])[CH:16]([CH3:18])[CH3:17])[CH:9]=1

참가 물질

6

반응물 4

HCID 70849Hantzsch esterHCID 774661,3-CyclopentanedioneHCID 145742L-ProlineHCID 547576553-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehyde

생성물 1

HCID 547578633-Hydroxy-2-(3-(2-((triisopropylsilyl)oxy)ethyl)benzyl)cyclopent-2-enone수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 14 (0.920 g, 3.0 mmol), 1,3-cyclopentadione (0.098 g, 1.0 mmol), and L-proline (0.005 mg) in dichloromethane (5 mL), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (0.253 g, 1.0 mmol) was added, and the resulting mixture was allowed to stir at rt for 12 h. The reaction mixture was directly purified by silica gel column chromatography using a gradient of ethyl acetate in hexanes as eluent, obtaining the title compound. Yield: 76%.

후처리

  1. customThe reaction mixture was directly purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-aeec9718dc6944e796d68c0a7954f05e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530520B2

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