1,3-Dimethyl-2-imidazolidinone → HCID 11858352, compound

HRID 1034538Notes

Reaction equation

HRID 1034538 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.CN1CCN(C)C1=O.[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:22][C:21]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH2:20])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 13669p-tert-Butylacetophenone

Product 1

HCID 11858352HCID 11858352, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-methoxybenzoyl chloride (2.35 g, 13.8 mmol), 0.65 g of cuprous chloride and 5.6 mL of 1,3-dimethyl-2-imidazolidinone were added to crude 4-tert-butylacetophenone trimethylsilylenol (6.7 mmol). After stirring the solution for 20 hours at room temperature, 1.4 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 twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1) giving 0.14 g of an uncolored oil corresponding to 1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate. Yield 7%.

Workup

  1. customThe first collected fraction was purified twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1)

Sources & evidence

ORD record
ord-8a6e53357f4644599400ba263895f79e
Source dataset
uspto-grants-2013_10
Patent number
US08545816B2

Reaction notes

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