MECHANISM
REACTION
|
wt/vol |
MW |
moles |
density |
equivs. |
yield |
|
|
I |
0.091 g |
386.71 |
0.0002 |
|
1.0 |
|
|
II |
0.059 g |
167.12 |
0.0004 |
|
1.5 |
|
|
III |
0.064 g |
206.33 |
0.0003 |
|
1.3 |
|
|
IV |
0.007 g |
122.17 |
0.0001 |
|
0.2 |
|
|
V |
5.0 mL |
– |
– |
|
|
|
|
VI |
0.122 g |
535.81 |
0.0002 |
|
|
(97%) |
Procedure: 25 mL 1-neck flask, stirbar, septum, N2 inlet
Dissolved 0.059 g II, 0.064 g of DCC and 0.007 g of DMAP in 4.0 mL of dry CH2Cl2. Stirred at rt. Added a solution of 0.091 g of alcohol I in 1.0 mL of CH2Cl2. Stirred for 45 min. The reaction mixture was then concentrated by rotary evaporation to ~ 0.5 mL. The product was isolated by flash chromatography on silica gel using 10:90 EtOAc-hexanes as eluant. The product was a clear, colorless oil.
1H NMR (CDCl3, 300 MHz) d 8.29 (d, J = 8.4 Hz, ArH), 8.20 (d, J = 8.4 Hz, ArH), 5.97 (dd, J = 15.8, 5.1 Hz, H3), 5.86 (dt, J = 15.8, 5.5 Hz, H2), 5.58 (dq, J= 15.4, 6.2 Hz, H7), 5.41 (dd, J = 15.4, 7.0 Hz, H6), 4.86 (d, J = 5.5 Hz, H1), 3.95 (dd(apparent t), J = 5.9 Hz, H4), 3.85 (dd(apparent t), J = 6.6 Hz, H5), 1.68 (d, J = 6.2 Hz, H8), 0.87 (s, SiC(CH3)3), 0.85 (s, SiC(CH3)3), 0.02 (s, SiCH3), 0.00 (s, Si(CH )2), -0.01 (s, SiCH3).
