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5th August 2014 @ 01:15

Cyclisation of JU 18-1 to synthesise prototypical ether compound. 

Github link#227

Reaction Scheme

Procedure

Started 12pm

JU 18-1 (2.01 g, 6.7 mmol) was stirred into CH2Cl2 (60 mL). PhI(OAc)(2.16 g, 6.7 mmol) was added and the resulting solution was stirred at room temperature for 3 h. Analysis by TLC showed that the reaction was complete.

TLC JU 19-1 50:50 EtOAc:Hex 3 h.JPG
 

The reaction was allowed to stir for a further hour while the work up of JU 15-2 was completed. The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (120 mL). The inorganic layer was extracted with CH2Cl2 (3 x 120 mL). The combined organic layers were dried over MgSO4, filtered and the solvent removed by rotary evaporation before the crude product was dried in vacuo (2.99 g, >100% crude yield).

1H NMR, crude, DMSO, 200 MHz

JU 19-1 crude 200 MHz.pdf
JU 19-1 crude.zip

The crude product was purified using the biotage isolera, see run details below.

JU 19-1_arch.pdf

The pure product was -description- (829 mg, 42%) and was analysed by 1H NMR which showed that the correct product had been formed, all expected peaks were present. The integrals do not match however, further analysis will be carried out. Frac 1 does not contain any identifiable material and is probably a mixture of iodobenzene, PIDA, impurities from 18-1 and 18-1. 

1H NMR, pure, DMSO, 300 MHz

JU 19-1 pure 300 MHz.pdf
JU 19-1 pure 13C 300 MHz.pdf
JU 19-1 pure.zip

1H NMR, frac 1, DMSO, 300 MHz

JU 19-1 frac 1 pure.pdf
JU 19-1 frac 1 pure.zip

 

HIRAC

HIRAC JU 19-1 signed.pdf

InChI strings

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H

SMILES

ClC1=CN=CC(N/N=C/C2=CC=C(OC(F)F)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

Linked Entries
Attached Files
Reaction Scheme JU 19-1.png
HIRAC JU 19-1 signed.pdf
JU 19-1 crude.zip
JU 19-1 frac 1 pure.zip
JU 19-1 frac 1 pure.pdf
JU 19-1 crude 200 MHz.pdf
JU 19-1 pure.zip
TLC JU 19-1 50:50 EtOAc:Hex 3 h.JPG
JU 19-1_arch.pdf
JU 19-1 pure 300 MHz.pdf
JU 19-1 pure 13C 300 MHz.pdf
JU 19-1 pure.zip