but-3-ynoxymethylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At −70° C., 2.56 ml of a 1.6 M butyllithium solution are added dropwise to a solution of 505 mg (3.15 mmol) of benzyl but-3-yn-1-yl ether in 10 ml of THF, and the mixture is stirred for 30 min. 500 mg (5.15 mmol) of 4-fluorobenzoyl chloride are added dropwise to this solution, and the temperature is allowed to rise to 0° C. After 1 h, 10 ml of a saturated ammonium chloride solution are added, and the reaction mixture is extracted with 3×50 ml of ethyl acetate. The combined organic phases are washed with water, dried over MgSO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 430 mg (45%) of the desired product; log P(HCOOH): 3.89; 1H-NMR (DMSO-d6): 8.15 (dd, 2H), 7.34 (m, 7H), 4.57 (s, 2H), 3.70 (t, 2H), 2.90 (t, 2H). to rise to 0° C After 1 h the reaction mixture is extracted with 3×50 ml of ethyl acetate The combined organic phases are washed with water dried over MgSO4 Purification by column chromatography on silica gel (cyclohexane/ethyl acetate)