dmso d 6 7 70 s 2h 8 29 dd j 8 8 2 2 hz 2h 8 36 d j 8 8 hz 2h 8 43 d j 2 2 hz 2h anal calcd for c 16 h 8 cl 2 n 2 o 5 379 15 c h n 2 5 bis 4 nitro 2 trifluoromethylphenyl furan compound 2e yield 74 fluffy golden needles mp 158 5 159 u00b0 c etoh 1 h nmr dmso d 6 7 38 s 2h 8 24 d j 8 7 hz 2h 8 57 d j 2 4 hz 2h 8 62 dd j 8 6 2 4 hz 2h anal calcd for c 18 h 8 f 6 n 2 o 5 446 26 c h n 2 5 bis 2 6 dimethyl 4 nitrophenyl furan compound 2f yield 65 yellow needles mp 156 5 157 5 u00b0 c dmf etoh h 2 o 1 h nmr dmso d 6 2 34 s 12h 6 85 s 2h 8 04 s 4h anal calcd for c 20 h 18 n 2 o 5 366 36 c h n 2 5 bis 4 amino 2 methylphenyl furan compound 3b to a suspension of the bis nitro derivative 2b 2 87 g in etoac 90 ml and dry etoh 10 ml was added pd c 10 0 40 g and the mixture was hydrogenated on a parr apparatus at an initial pressure of u02dc 50 psi after the uptake of hydrogen subsided generally 3 6 hours the resulting solution was filtered over celite and the pale yellow to colorless filtrate was concentrated in vacuo to near dryness to give after dilution with hexanes.