HCID 18436351, compound → HCID 18436342, compound

Participants

Reaction Conditions

Reaction Steps

To the above mixture of 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-1-enyl]-phenol and 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-2-enyl]-phenol (380 mg) in DCM (10 mL) at −10° C. was added TiCl4 (0.180 mL) and the mixture was stirred for 3 h at −10° C. The reaction mixture was diluted with ethyl acetate/H2O (200/100 mL). The organic layer was dried and purified on SiO2 to yield two products 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-1-enyl]-phenol and 4-[2-ethyl-4-hydroxymethyl-6-(4-methoxy-phenyl)-3-methyl-cyclohexyl]-phenol.

Provenance & Evidence