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

HRID 1033531Notes

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 deoxyanisoin, 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. After the completion of reaction, the reaction mixture was allowed to stand at room temperature with addition of n-hexane. The product separating out was filtered off and dissolved with 1000 ml of ethyl acetate and 300 ml of 3N sulfuric acid. The organic layer was collected, washed with 3N sulfuric acid and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The organic layer was concentrated at a reduced pressure, giving 153 g (yield 90%) of the above-identified compound as an oily product.

Workup

customAfter the completion of reaction
customThe product separating out
filtrationwas filtered off
dissolutiondissolved with 1000 ml of ethyl acetate and 300 ml of 3N sulfuric acid
customThe organic layer was collected
washwashed with 3N sulfuric acid
dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
concentrationThe organic layer was concentrated at a reduced pressure

Sources & evidence

ORD record: ord-306b715cc5df4f70a1c78c1e400da16f
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310926

Reaction notes

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