1,3-Dimethyl-2-imidazolidinone → HCID 11858351, compound

HRID 1034537Notes

Reaction equation

HRID 1034537 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCN(C)C1=O.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)=[O:24].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:24][C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH2:22])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 74764'-MethoxyacetophenoneHCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 11858351HCID 11858351, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-tert-butylbenzoyl chloride (1.78 g, 9 mmol), 0.47 g of cuprous chloride and 4 mL of 1,3-dimethyl-2-imidazolidinone were added to crude 4-methoxyacetophenone trimethylsilylenol (4.3 mmol). After stirring the solution for 21 hours at room temperature, 1 mL of triethylamine and 10 mL of chloroform were added. Then the solution was chromatographied through flash silica column (hexane/ethyl acetate 10:1). The first collected fraction was purified by flash chromatography (hexane/dichloromethane 3:2) giving 0.34 g of 1-(4-methoxyphenyl)-vinyl 4-tert-butylbenzoate. Yield 25%.

Workup

  1. customThe first collected fraction was purified by flash chromatography (hexane/dichloromethane 3:2)

Sources & evidence

ORD record
ord-c1a329476a5b471da018a55d11824810
Source dataset
uspto-grants-2013_10
Patent number
US08545816B2

Reaction notes

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