Triethylamine → 2,2-dimethyl-propionic acid 4-[1-furan-3-yl-meth-(E)-ylidene]-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopent-1-enyl ester

HRID 336087Notes

Reaction equation

HRID 336087 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[C:7]2/[C:8](=[O:22])[CH:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:10](=[O:12])[CH2:11]/2)=[CH:2]1.C(N(CC)CC)C.[CH3:30][C:31]([CH3:36])([CH3:35])[C:32](Cl)=[O:33]>ClCCl>[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[C:7]2/[C:8](=[O:22])[C:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:10]([O:12][C:32](=[O:33])[C:31]([CH3:36])([CH3:35])[CH3:30])[CH2:11]/2)=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 666838824-[1-Furan-3-yl-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

Product 1

HCID 666830282,2-dimethyl-propionic acid 4-[1-furan-3-yl-meth-(E)-ylidene]-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopent-1-enyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[1-furan-3-yl-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (50 mg) in dichloromethane (2 ml) is added triethylamine (118 μl), followed by trimethylacetyl chloride (105 μl) and the resulting suspension allowed to stir at room temperature for 3 hours. The crude reaction mixture is then purified by automated flash chromatography to give 2,2-dimethyl-propionic acid 4-[1-furan-3-yl-meth-(E)-ylidene]-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopent-1-enyl ester.

Workup

  1. customThe crude reaction mixture
  2. customis then purified by automated flash chromatography

Sources & evidence

ORD record
ord-654a72c82ac94d5992d546d512ed2b40
Source dataset
uspto-grants-2014_11
Patent number
US08889595B2

Reaction notes

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