Trifluoroacetic acid → (+/-)-7-(4-Fluorophenoxy)-6-(hydroxy)-heptan-al

Participants

Reaction Steps

(±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)heptan-1-al 45 (2 g, 6.1 mmol) and 2 ml of trifluoroacetic acid are added to 10 ml of chloroform. The reaction mixture is stirred for 24 hours and then is neutralized with 1% aqueous NaOH. The organic layer is washed with water, brine, dried (Na2SO4), concentrated. The crude trifluoroacetyl-aldehyde 46 is then dissolved in MeOH:H2O (1:1) and solid K2CO3 is added to maintain pH 8. The reaction is complete is approximately 15 minutes, as monitored by TLC (ethyl acetate:hexane 3:7). Methanol is removed in vacuo and remaining solution is extracted with ethyl acetate to give (±)-7-(4-fluorophenoxy)-6-(hydroxy)-heptan-al 47 (1.2 g, 82%).

Provenance & Evidence