Methacrylic Acid → HCID 20745891, compound

Participants

Reaction Conditions

Reaction Steps

382 mg (2.5 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5) (DBU) in 4 ml N,N-dimethylformamide were added dropwise to a solution of 200 mg (2.3 mmol) 2-methylacrylic acid in 8 ml N,N-dimethylformamide over a period of 35 minutes. After addition of 4 mg phenothiazine, 1.5 g (2.3 mmol) (E)-3-[4-[[3-[(6-chlorohexyl)oxy]-5-[[2-methoxy-4-[(E)-2-(methoxycarbonyl)vinyl]phenoxy]methyl]benzyl]oxy]-3-methoxyphenyl]acrylic acid methyl ester and 84 mg tetrabutylammonium iodide the resulting mixture was stirred at 80° C. for 25 hours. The reaction mixture was poured into 50 ml of an ice cold 1 M HCl solution. The aqueous phase was extracted three times with 50 ml ethyl acetate. The organic phase was washed with 50 ml of a saturated sodium bicarbonate solution and repeatedly with water, dried over magnesium sulfate, filtered and concentrated by vacuum evaporation. Purification of the residue by column chromatography on 275 g silica gel using hexane:ethyl acetate (1:1) as eluent yielded 1.46 g (90%) of 2-methylacrylic acid 6-[3,5-bis[[2-methoxy-4-[(E)-2-(methoxycarbonyl)vinyl]phenoxy]methyl]phenoxy]hexyl ester as a yellowish oil.

Provenance & Evidence