Tetrabutylammonium Fluoride → [(3-Hydroxyphenyl)(2-phenoxyethoxy)methylene]-5-chloroadamantane

Participants

Reaction Steps

To a solution of 4.9 parts of alkene (64) in 75 mL of THF was added 5.0 parts of 70% mixture of tetra-n-butylammonium fluoride in 25 mL of THF over a period of 15 minutes. The reaction mixture was stirred for two hours. TLC on silica gel plate showed the formation of new product. The solvent was evaporated under reduced pressure and the oily material was dissolved in 150 mL of ethyl acetate and washed with two times with 200 mL of water. After drying over anhydrous sodium sulfate, the solvent was evaporated and the oily product was purified on silica gel column. TLC on silica gel plate of the fractions were checked and the combined organic solvent was evaporated, yield 2.5 parts. The structure of the product was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Provenance & Evidence