Tetrabutylammonium Fluoride → (4E,6E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethylnona-4,6-dien-3-ol

Participants

Reaction Steps

850 mg (1.3 mmol) of (4E,6E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-3-ethylnona-4,6-dien-3-ol are dissolved in 20 mL of anhydrous THF. 3.9 mL (3.9 mmol) of 1 M tetrabutylammonium fluoride solution are then added and the medium is stirred for 4 hours. After the usual treatment, the residue is purified by chromatography on silica gel (eluent: 2 heptane/8 ethyl acetate). (4E,6E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethylnona-4,6-dien-3-ol is obtained in the form of a yellow oil (m=340 mg; Y=63%).

Provenance & Evidence