Ammonium Chloride → HCID 23069064, compound

HRID 1373458Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:19])/[CH:12]=[CH:13]/[C:14]([O:16]CC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:20]1([Mg]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:19])/[CH:12]=[CH:13]/[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 10 °C

Procedure

Into a 200 ml four-neck flask were added 10 g (0.038 mol) of ethyl (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate obtained in Example 1 and 50 ml of tetrahydrofuran under a nitrogen atmosphere, and 22.5 ml (0.045 mol) of a tetrahydrofuran solution of 32% phenylmagnesium bromide was slowly added dropwise so as to maintain inner temperature at 10° C. or lower. Then, after 1 hour of stirring at room temperature, the whole was again cooled and 50 ml of a 5% ammonium chloride aqueous solution was added to effect hydrolysis. After liquid separation, the resulting organic layer after completion of the reaction was washed with 50 ml of a 10% sodium bicarbonate aqueous solution and then with 50 ml of water. After the solvent was removed by evaporation under reduced pressure, the residue was crystallized from 10 ml of ethanol to obtain 8.8 g (yield 78.0%) of the aimed compound. As a result of HPLC analysis, the purity was found to be 99.2%.

Workup

temperaturethe whole was again cooled
customAfter liquid separation
washthe resulting organic layer after completion of the reaction was washed with 50 ml of a 10% sodium bicarbonate aqueous solution
customAfter the solvent was removed by evaporation under reduced pressure
customthe residue was crystallized from 10 ml of ethanol

Sources & evidence

ORD record: ord-2072189fdac541b89ef4cc7ec2d7680c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07161022B2

Reaction notes

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