Triethylsilane → HCID 12508514, compound

Participants

Reaction Steps

Trifluoromethanesulphonic acid (0.2 ml, 2.3 mM) in dichloromethane (0.5 ml) was added dropwise to a solution of the epsilon-lactone of 3-(2-hydroxy-4,6-dimethylbenzoyl)propionic acid, [m.p. 77° C.; prepared by the method described in Acta. Chem. Scand. 1972, 26, 2372, but starting from 3-(2-hydroxy-4,6-dimethylbenzoyl)propionic acid, itself prepared as described in Liebigs Ann. Chem. 1985, 560] in dichloromethane (1 ml) at 0° C. under argon, followed by a solution of triethylsilane (200 mg, 1.7 mM) in dichloromethane (0.5 ml). After 5 minutes, a further portion of trifluoromethanesulphonic acid (0.2 ml, 2.3 mM) in dichloromethane (0.5 ml) was added followed by triethylsilane (200 mg; 1.7 mM) in dichloromethane (0.5 ml). The reaction mixture was stirred for 2 hours at ambient temperature, then poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The combined extracts were washed with brine, dried (Na2SO4), and the solvent was removed by evaporation. The residual oil was purified by flash chromatography, eluting with hexane/dichloromethane (1:1 v/v increasing in polarity to 1:3 v/v), giving the epsilon-lactone of 4-(2-hydroxy-4,6-dimethylphenyl)butyric acid (C) as a colourless oil; NMR: 2.10(2H,tt), 2.29(6H,s), 2.43(2H,t), 2.79(2H,t), 6.75(1H,s), 6.86(1H,s); I.R (thin film) 1720 cm-1.

Provenance & Evidence