wt/vol

 

wt/vol

MW/conc.

moles

density

equivs.

yield

I

6.632 g

206.33

0.0321

 

1.0

 

II

20.0 mL

65%

 

 

2.0

 

III

200 mL

-

-

 

 

 

IV

6.351 g

208.25

0.0305

 

 

(95%)

 

Procedure:  500 mL 1-neck flask, stirbar, septum, N2 inlet

                  Dissolved 6.632 g of propargyl alcohol I in 200 mL of dry THF.  Stirred;  cooled to 0 C.  Added 20.0 mL of Red-Al (65 w/w% in toluene) dropwise.  Vigorous gas evolution was observed.  After 55 min the reaction was quenched with sat. aq. Na/K tartrate and stirred for 16 h.  Two clear layers were obtained which were separated and the aqueous layer was extracted with Et2O.  The organic layers were combined and dried over MgSO4, filtered and the solvent was removed by rotary evaporation.  The product was isolated by flash chromatography on silica gel using Et2O as eluant.  The product was a clear, pale yellow oil.