Trimethyl orthoformate → HCID 68863774, compound

Participants

Reaction Steps

A soln. of 1.5 g of 5-isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (7.3 mmol), 1.4 g para-toluenesulfonic acid mono hydrate (7.4 mmol 1 eq.), and 0.78 g trimethylorthoformate (7.4 mmol, 1 eq.) in 50 ml methanol was heated at 60° C. for 66 h. The reaction mixture was then cooled and poured into aq. sat. NaHCO3 soln. (20 ml). Extraction with MTBE (2×80 ml) followed by washing of the aq. phases with H2O and aq. sat. NaCl soln., drying of org. phases (MgSO4) led to 1.8 g of crude product. FC (SiO2, Hexane/MTBE 30:1) gave 1.7 g (92%) of compound 5 as colorless liquid. The boiling point of the end product is 130° C. at 0.08 mbar. Rf (hexane/MTBE 8:1) 0.57.

Provenance & Evidence