Réaction #155385

Équation de réaction

sodium hydride

trans,trans-farnesol

→

bisfarnesyl ether

Rendement 80.0%

Solvants

THF

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred for 20 h
2. 2
   AutreThe reaction was quenched with 2 mL of 1M HCl
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   Lavagewashed successively with water and brine
5. 5
   Séchagedried over anhydrous MgSO4
6. 6
   AutreThe crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc

Mode opératoire

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).

Source