PREPARATION OF CYCLOPROPANE DERIVATIVE

PREPARATION OF CYCLOPROPANE DERIVATIVE

Using NaH and Pd(0)

Procedure

1. Dissolve Imine and butene in THF. Stir (N₂)

2. Add Pd(OAc)₂ and Ph₃P (as neat to form Pd(0)) [1]

3. Stir the mixture at R.T. for 30 min

4. Add slowly and portionally NaH (60% in mineral oil) over 45 min [2]

5. Stir the reaction mixture at R.T for 1 hr [3]

6. Quench reaction w/ ice cold water and dilute w/ EtOAc

7. Filter thru Celite [4]. Wash filtrate w/water and brine

8. Dry organic layer w/ MgSO₄. Filter

9. Concentrate in vacuo ® crude as brownish oil

10. Chromatograph w/ 0% ® 5% EtOAc/Hex [5]

11. NMR w/ CDCl₃. Yield 70% as yellow oil [6]

G Notes:

[1] Color change from light to darker yellowish solution

[2] Slow addition of NaH is very important. Gas , color change from yellow to green then brownish

[3] Follow reaction by TLC w/10% EtOAc/Hex

[4] Wash Celite pad w/EtOAc

[5] Dissolve the crude in Et₂O

[6] 10% of Didebromination may obtain

Synlett 1996, November, p1067