Three-component Condensation / MAC Reagent

α -Acetoxyacetic Acid Methyl Esters; General Procedures Method A (21a-e)

H-MAC-Ac (16; 29.8 mg, 0.24 mmol, 1.2 equiv) was added to a solution of 20 (0.20 mmol, 1.0 equiv) and base (0.30 mmol, 1.5 equiv) in anhyd MeOH (5 mL) at r.t., and the mixture was stirred for 3 h at r.t.. The resulting solution was concentrated in vacuo, and the residue was purified by column chromatography and, optionally, crystallization.

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20: 4-Methylbenzaldehyde
base: Imidazole

Methyl Acetoxy(4-methylphenyl)acetate (21a)
Purified by column chromatography [silica gel, hexane-EtOAc (9:1)] and crystallization (Et2O/hexane) as colorless crystals; yield: 41.3 mg (0.186 mmol, 93%).

2009
One-Portion Synthesis of 2-Acetoxy Carbonyl Compounds from Aldehydes by Using an Acetylated Masked Acyl Cyanide
10.1055/s-0028-1088044

2004
MAC反応剤　簡便な1炭素増炭型3成分連結反応

2-(Acetyloxy)propanedinitrile / 6625-70-3