Ethyl Acetoacetate → 3-(2'-Oxo-3'-ethoxycarbonylbutyl)-benzophenone

HRID 1731182Notes

Reaction equation

[CH3:1][CH2:2][O-:3].[Na+].[Na].[C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.BrC[C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][CH:30]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>C1C=CC=CC=1>[O:3]=[C:2]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6])[CH2:1][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:20]([C:19]1[CH:18]=[CH:17][CH:30]=[CH:29][CH:28]=1)=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

Dry sodium ethylate prepared from 2.51 g of sodium was added to 125 ml of anhydrous benzene and 13.5 ml of ethyl acetylacetate at 20° C and after heating at 100° C for 15 minutes, 27.5 g of 3-bromomethyl-benzophenone were added all at once. The reaction mixture was refluxed for 3 hours and after cooling to 20° C, the benzene solution was washed twice with 25 ml of 2N hydrochloric acid and then with water until the wash water was neutral. The solution was dried over sodium sulfate and evaporated to dryness under reduced pressure to obtain 33.8 g of raw product which was chromatographed over silica gel and was eluted with a 50-50 mixture of ether-petroleum ether (B.P. of 40°-60° C) to obtain 15.3 g of 3-(2'-oxo-3'-ethoxycarbonyl-butyl)-benzophenone in the form of a marron resin which was used as is for the next step.

Workup

temperatureThe reaction mixture was refluxed for 3 hours
temperatureafter cooling to 20° C
washthe benzene solution was washed twice with 25 ml of 2N hydrochloric acid
dry with materialThe solution was dried over sodium sulfate
customevaporated to dryness under reduced pressure
customto obtain 33.8 g of raw product which
customwas chromatographed over silica gel
washwas eluted with a 50-50 mixture of ether-petroleum ether (B.P. of 40°-60° C)

Sources & evidence

ORD record: ord-d549663478cf437db3d6959472429d59
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03995056

Reaction notes

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