Sodium hydride → Bisfarnesyl ether

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To 81 mg (2.03 mmole, 2 eq) of 60% sodium hydride (washed with anhydrous hexanes to remove mineral oil) in 1 mL of anhydrous THF under an argon atmosphere at 0° C., 228 mg (1.02 mmol) of trans,trans-farnesol in 1 mL of anhydrous THF was added. The mixture was stirred for 10 min, then 438 mg (1.53 mmol, 1.5 eq) of trans,trans-farnesol bromide was added in 0.5 ml of anhydrous THF. The mixture was stirred for 20 h and allowed to warm to 25° C. The reaction was quenched with 2 mL of 1M HCl, diluted with EtOAc, washed successively with water and brine and dried over anhydrous MgSO4. The crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc:hexanes to afford 174 mg (40%) of bisfarnesyl ether that had NMR and mass spectral data identical to that of material produced in enzymatic reactions (FIG. 7).

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