Water → HCID 24751629, compound

Participants

Reaction Conditions

Reaction Steps

(E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-en-1-ol (29.7 mg, 0.097 mmol) in AcCN (0.5 mL) with 2 drops of H2O was cooled to 0° C. CAN (114.7 mg, 0.209 mmol) was dissolved into AcCN (0.2 mL) and H2O (0.5 mL) and added to a stirred solution of alcohol at 0° C. The reaction was stirred at 0° C. for 1 h and H2O (2 mL) and EtOAc (2 mL) was added, the layers separated and the aqueous phase extracted 3×2 mL EtOAc. The combined organics were washed 2×2 mL saturated brine, dried over anhydrous Na2SO4 and concentrated to a yellow oil. Flash chromatography yielded (E)-2-(7-hydroxy-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione (2.2 mg) as a yellow oil (8.2%). 13C NMR (100 MHz, CDCl3) δ 187.9, 187.0, 143.1, 140.4, 104.3, 134.0, 119.7, 77.2, 62.9, 39.3, 32.3, 25.6, 24.0, 16.2, 12.4, 12.3, 12.2

Provenance & Evidence