wt/vol

 

wt/vol

MW/conc.

Moles

density

equivs.

yield

I

1.840 g

300.55

0.0061

 

1.0

 

II

18.3 mL

1.0 M

0.0183

 

3.0

 

III

40 mL

-

-

 

 

 

IV

1.038 g

186.29

0.0056

 

 

(91%)

 

Procedure:  100 mL 1-neck flask, stirbar, cap

                  Dissolved 1.840 g alcohol I in 40 mL of THF.  Stirred at rt.  Added 18.3 mL of TBAF (1.0 M in THF, water content ~5 wt. %, Aldrich).  After 3 h, quenched with sat. aq. NH4Cl.  Extracted with EtOAc.  The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation.  The product was isolated by flash chromatography on silica gel using 75:25 Et2O-hexanes.  The product was a clear, pale yellow oil. 

 

1H NMR (CDCl3, 400 MHz) d 5.76 (dq, J = 15.4, 6.5 Hz, H2), 5.46 (ddq, J = 15.3, 7.3, 1.6 Hz, H3), 3.83 (m, H4), 3.41 (m, H5), 2.11 (b, OH), 2.02 (b, OH), 1.71 (dd, J = 6.5, 1.1 Hz, H1), 1.53-1.22 (m, CH2s), 0.86 (t, J = 7.0 Hz, H11).