Sodium hydride → Ethyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]-2-propenoate

HRID 432976Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH2:7][O:8][CH2:9][CH2:10]P(OCC)(OCC)=O)[CH3:4].[CH2:20]([O:22][CH:23]([O:34][CH2:35][CH3:36])[CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[CH3:21]>C1COCC1>[CH2:9]([O:8][C:7](=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH:23]([O:34][CH2:35][CH3:36])[O:22][CH2:20][CH3:21])=[CH:27][CH:28]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:19])[CH3:10]

Participants

Conditions

Temperature: 15 °C

Procedure

To a stirred suspension of sodium hydride (756 mg, 32 mmol, 95%) in dry THF (60 mL) was added a solution of ethyl(diethylphosphono)ethoxyacetate (6.20 g, 23.1 mmol) in THF (20 mL) at 0-5° C. dropwise and stirred for 30 min at 5-25° C. To the reaction mixture was added a solution of 4-[(2,2-diethoxy)ethoxy]benzaldehyde (5.0 g, 21.0 mmol) in THF (10 mL) at 25° C. and stirred further for 30 min. After completion of the reaction (TLC monitored), THF was removed and the resultant residue was diluted with water (100 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated to yield the title compound (6.5 g, 88%) as a mixture of E/Z isomers.

Workup

stirringstirred further for 30 min
customwas removed
additionthe resultant residue was diluted with water (100 mL)
extractionextracted with ethyl acetate (3×25 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-a6dc36c3c019443992263c68c99919c2
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664411B2

Reaction notes

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