Boron trifluoride → Butyl ether

Participants

Reaction Steps

Compound (13) is prepared as follows: To a solution of 18.9 g t.butyltrichloroacetimidate in 50 ml cyclohexane is added a solution of 12.1 g geraniol (10) in 50 ml cyclohexane. After external cooling in ice is added dropwise in 15 min 0.8 ml BF3 -etherate. The reaction mixture is stirred at room temperature for 2 hours. Then 1.0 g NaHCO3 is added and the mixture is stirred for 10 min. The precipitate is filtered off and washed with hexane. After separation, washing with 5% aqueous NaHCO3 -solution and water successively, drying and evaporation to dryness, the organic phase yields 17.3 g of a product. This product is purified by flash chromatography; the desired t.butylether (13) is obtained in a yield of 11.43 g (69%). Identification by NMR: 1H-NMR(CDCl3); δ: 5.33 (t.1H); 5.09 (t.1H); 3.92 (d.2H); 2.15-1.95 (4H); 1.67 (s. 3H); 1.66(s.-3H); 1.59 (s.3H); 1.23 (s.9H).

Provenance & Evidence