Sodium hydride → (E)-ethyl 3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoate

HRID 2368866Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(OP(OCC)OCC)C.[H-].[Na+].[CH3:26][O:27][CH2:28][O:29][C:30]1[C:37]([CH3:38])=[CH:36][C:33]([CH:34]=O)=[CH:32][C:31]=1[CH3:39]>CN(C=O)C.C(OCC)(=O)C>[CH3:26][O:27][CH2:28][O:29][C:30]1[C:37]([CH3:38])=[CH:36][C:33](/[CH:34]=[CH:2]/[C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:32][C:31]=1[CH3:39]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 3-(chloromethyl)benzoate (1.192 g, 6 mmol) and triethylphosphite (1.273 mL, 7.2 mmol) were heated to 150° C. for 4 hours. The reaction mixture was cooled to 0° C. and then DMF was added. NaH (60% in oil, 0.252 g, 6.3 mmol) was added to the solution at 0° C. After stirring for 20 minutes, the solution of 4-(methoxymethoxy)-3,5-dimethylbenzaldehyde (4-MOMO-3,5-dimethylbenzaldehyde; 0.583 g, 3 mmol) in DMF was added to the mixture dropwise at 0° C. After 18 hours, the mixture was diluted with ethyl acetate (EtOAc) and the solution was washed with 10% citric acid and brine. After drying on Na2SO4, the organic layer was filtered and concentrated under reduced pressure. The compound was purified by column chromatography (9.5:0.5 Hexane:EtOAc) to afford (E)-ethyl 3-[4-(methoxymethoxy)-3,5-dimethylstyryl]-benzoate (0.726 g, 71%).

Workup

waitAfter 18 hours
washthe solution was washed with 10% citric acid and brine
customAfter drying on Na2SO4
filtrationthe organic layer was filtered
concentrationconcentrated under reduced pressure
customThe compound was purified by column chromatography (9.5:0.5 Hexane:EtOAc)

Sources & evidence

ORD record: ord-9996738b0cb245ff8c5d038f5fe020eb
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703815B2

Reaction notes

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