HCID 53666689, compound → HCID 54438093, compound

Participants

Reaction Steps

Activated manganese dioxide (40 g) was added to a solution of methyl 7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate (6.8 g, 21.3 mmol) in chloroform (600 mL) and the black suspension was vigorously stirred at ambient temperature for 20 hours. After filtration and evaporation of the solvent the residual amber oil (4.5 g, 1 major spot on TLC with Rf 0.61 on Whatman MK6F silica using CHCl -MeOH; 19:1 as eluent) was chromatographed on a Still column to obtain the product (3.9 g, 58%) as a pale yellow oil which solidified on standing, m.p. 77°-79° C.; NMR (CDCl3) δ: 2.57 (2H, d, J=6Hz, --C2CO2 --), 2.93 (2H, d, J=6Hz, --CH2 --CO--), 3.70 (3H, s, --CO2CHp3), 4.4-4.8 (H, m, --CH(OH)--), 6.67 (H, d, J=16 Hz, =CH--CO), 7.1-7.7 (3H, m. ArH), 7.93 (H, d, J=16 Hz, =CH).

Provenance & Evidence