Triethyl ethane-1,1,2-tricarboxylate → Dimethyl trans-1-(Carboethoxymethyl)-5-(3-hydroxy-3-methyl-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate

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Reaction Steps

To a solution of triethyl 1,1,2-ethanetricarboxylate (1.36 g) in 3 ml of methanol, a freshly prepared solution of sodium methoxide (from 0.126 g of sodium and 6 ml of absolute methanol) is added. The mixture is heated to 80°. A solution of dimethyl trans-(3-methyl-3-hydroxy-1-octenyl)cyclopropane-1-1-dicarboxylate (1.7 g) is gradually added and the resulting mixture stirred for an additional 15 min. The methanol is removed by distillation at reduced pressure. The residue is then heated at 100° for 45 min. Thereafter the mixture is cooled in an ice bath and rendered neutral with acetic acid. The mixture is extracted with ether. The extract is dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel using ethyl acetate/benzene (1:4) as eluant gives the title compound, νmaxfilm 3350, 1727 cm-1.

Provenance & Evidence