Methanol → HCID 86619080, compound

Participants

Reaction Steps

To a solution of 10.0 g (40 mmol) (E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enoic acid [H. S. Corey, J. R. D. Cormick, W. E. Swensen, J. Am. Chem. Soc. 1964, 86, 1884], isomeric purity of 95%, in 100 ml MTBE were added at r.t. 6.64 g (40 mmol) (S)-(+)-mandelic acid methyl ester [α]D=+144.9 (c=1.04, MeOH) and 1.0 g DMAP. Then a solution of 8.24 g (40 mmol) DCC in 100 ml MTBE was added and the reaction mixture stirred for 2 h. After addition of 1 ml MeOH and 1 ml HTDNF the mixture was stirred for 30 min, filtered and the residue washed with MTBE. The combined organic phases were concentrated in vacuo and the residue (18.0 g) was purified by flash chromatography (silicagel, hexane/MTBE 9:1) affording 14.0 g (88%) 4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enoic acid (S)-methoxycarbonyl-phenyl-methyl ester (11) in form of a colorless oil.

Provenance & Evidence