Water → ethyl (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoate

HRID 16649Notes

Reaction equation

CC(C)([O-])C.[K+].C(OP([CH2:15]/[C:16](/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])(OCC)=O)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=1[C:39](=[O:42])[CH:40]=O.O>O1CCCC1>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=1[C:39](=[O:42])/[CH:40]=[CH:15]/[C:16](/[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

1.32 g (11.8 mmol) of potassium tert-butoxide and 30 ml of tetrahydrofuran are mixed together at 25° C. A solution of 3.85 g (11.8 mmol) of ethyl (E)-4-(diethoxyphosphoryl)-3-phenylbut-2-enoate in 30 ml of tetrahydrofuran is then added dropwise. A solution of 3 g (15.4 mmol) of (2,5-dimethoxyphenyl)-2-oxoacetaldehyde dissolved in 30 ml of tetrahydrofuran is added dropwise, at 25° C. The mixture is stirred for 16 hours at 25° C. It is poured into water and extracted with ether. The organic phase is dried (Na2SO4) and the solvents are evaporated off under reduced pressure. The 4 g of product obtained are purified by flash chromatography (80/20 heptane/ethyl acetate) (yellow oil: 0.46 g).

Workup

additionis added dropwise, at 25° C
extractionextracted with ether
dry with materialThe organic phase is dried (Na2SO4)
customthe solvents are evaporated off under reduced pressure

Sources & evidence

ORD record: ord-67656348565c4bc5b7f7d64001551b6b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737176B2

Reaction notes

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