Methyl vinyl ketone → {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl]oxy}acetonitrile

HRID 569304Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:21])[C:11]([Cl:20])=[C:12]([O:16][CH2:17][C:18]#[N:19])[CH:13]=2)[C:8]1=[O:22])(=[O:3])[CH3:2].N12CCCC1=CCCN2.[CH:32]([C:34]([CH3:36])=[O:35])=[CH2:33].C(OCC)(=O)C>O1CCCC1.N12CCCC1=CCCN2.C(O)(=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1([CH2:33][CH2:32][C:34](=[O:35])[CH3:36])[CH2:15][C:14]2[C:9](=[C:10]([Cl:21])[C:11]([Cl:20])=[C:12]([O:16][CH2:17][C:18]#[N:19])[CH:13]=2)[C:8]1=[O:22])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

{[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetonitrile (3.42 g, 10 mMole) is dissolved in tetrahydrofuran (30 ml), warmed to 40° C. and diazabicyclo[4.3.0]non-5-ene (50 microliters) added. Then methyl vinyl ketone (1.2 g, 17 mMole) is added and the mixture stirred at 50°-52° C. for two hours. More methyl vinyl ketone (600 mg) and diazabicyclo[4.3.0]non-5-ene (2 drops) are added and stirring and heating continued for another 2 hours. The solution is cooled, treated with ethyl acetate (50 ml) and poured into ice water (250 ml) containing acetic acid (1 ml). The organic layer is separated and the aqueous layer extracted first with methylene chloride and then with ether. The combined organic layers were dried over MgSO4 and the solvent removed by evaporation in vacuo to give the desired product.

Workup

stirringstirring
temperatureheating
waitcontinued for another 2 hours
temperatureThe solution is cooled
customThe organic layer is separated
extractionthe aqueous layer extracted first with methylene chloride
dry with materialThe combined organic layers were dried over MgSO4
customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record: ord-a44c4640c76245ea9b3702fd97263d87
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04731471

Reaction notes

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