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

HRID 41146

Reaction equation

HRID 41146 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-aeec9718dc6944e796d68c0a7954f05e
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Linked notes

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