Dimethylformamide dimethyl acetal → 6-Dimethylaminomethylene-4,4-diphenylcyclohex-2-enone

HRID 1243853Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]1([C:15]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[CH:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C=O>[CH3:6][N:4]([CH:3]=[C:19]1[C:18](=[O:21])[CH:17]=[CH:16][C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:20]1)[CH3:5]

Participants

Conditions

Temperature: 20 °C

Procedure

4.77 g of N,N-dimethylformamide dimethyl acetal are added to a solution of 2.48 g of 4,4-diphenylcyclohex-2-enone in 20 Cm3 of N,N-dimethylformamide. The mixture is refluxed for about 4 hours. After cooling to a temperature in the region of 20° C., the solution is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 50 cm3 of diisopropyl ether and allowed to precipitate for about 20 hours at a temperature in the region of 20° C. The solid is drained by suction, washed with three times 10 cm3 of diisopropyl ether and then dried under reduced pressure (13 kPa) over potassium hydroxide at a temperature in the region of 20° C. 1.7 g of 6-dimethylaminomethylene-4,4-diphenylcyclohex-2-enone are thus obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

temperatureThe mixture is refluxed for about 4 hours
concentrationthe solution is concentrated to dryness under reduced pressure (13 kPa)
customto precipitate for about 20 hours at a temperature in the region of 20° C
washwashed with three times 10 cm3 of diisopropyl ether
dry with materialdried under reduced pressure (13 kPa) over potassium hydroxide at a temperature in the region of 20° C

Sources & evidence

ORD record: ord-f10d5c490f904ada9c2731611ed62f1a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119115B2

Reaction notes

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