tert-Butanol → Methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate

HRID 2260744Notes

Reaction equation

C(O)(C)(C)C.[C:6]1([C:14]([CH2:16][C:17]2[CH:24]=[CH:23][C:20]([O:21][CH3:22])=[CH:19][CH:18]=2)=[O:15])[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[CH:8][CH:7]=1.CC(C)([O-])C.[K+].CO[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[O:36]>CCCCCC>[CH3:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:14]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[CH:12][CH:13]=2)=[O:15])=[CH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 430 ml of tert-butanol were added 128 g of deoxyanisoine, 67.3 g of potassium tert-butoxide and 116 g of methyl 3-methoxyacrylate, and the mixture was stirred at 70° C. for 3 hours. To the resulting mixture was added n-hexane, and the mixture was allowed to stand at room temperature. A formed precipitate was filtered and dissolved by adding 1,000 ml of ethyl acetate and 300 ml of 3N-sulfuric acid. An organic layer was separated, washed with 3N-sulfuric acid and saturated brine and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give 153 g (yield 90%) of methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate as an oil.

Workup

customto stand at room temperature
filtrationA formed precipitate was filtered
dissolutiondissolved
additionby adding 1,000 ml of ethyl acetate and 300 ml of 3N-sulfuric acid
customAn organic layer was separated
washwashed with 3N-sulfuric acid and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-aa86a50b8b174aefa18310774bffabf6
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478856

Reaction notes

Loading…