Methyl acetoacetate → Methyl 4-(2-ethoxy-2-oxoethyl)-3-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-3-methylbenzoate (1.5 g, 6.55 mmol), methyl 3-oxobutanoate (0.99 g, 8.51 mmol) and K3PO4 (4.17 g, 19.6 mmol) were mixed with Pd(OAc)2 (15 mg) and di-tert-butyl(2′-methyl-[1,1′-biphenyl]-2-yl)phosphine (39 mg), and diluted with toluene (25 ml). The resultant mixture was simply degassed via vacuum and charged with argon. Then it was heated at 90° C. for 24 h and at 110° C. for 5 hours. After aqueous work-up with EtOAc, the desired product-methyl 4-(2-ethoxy-2-oxoethyl)-3-methylbenzoate was isolated by column chromatography, eluting with EtOAc/Hexane (1/3), as oil (366 mg, 25%).

Provenance & Evidence