Pyrrole → HCID 18694739, compound

Heptafluorobutyraldehyde hydrate (5.0 g, 23 mmol) was placed in a 100 mL Schlenk flask. This was frozen with liquid nitrogen and an inert atmosphere was established. Against an outflow of nitrogen, dried pyrrole (0.694 mL, 10 mmol) and sodium hydroxide (2.25 g, 56 mmol) were added. The flask was wrapped in foil and the mixture was stirred for 2 days. The volatiles were removed by vacuum, leaving a light brown, oily solid. The solid was dissolved in 40 mL of water and the solution was extracted (4×50 ml) with methylene chloride. The organic layers were dried over sodium sulfate and then evaporated to dryness under vacuum to an oily brown solid (38%), which proved to be a diastereomeric mixture of the desired products. 1H NMR of recrystallized product (CDCl3, 360 MHz) d 8.78 (broad s, 1 H); 6.28 (d, 2H, J=2.8 Hz); 5.128 (dd, 2 H, J1=117 Hz, J2=8 Hz); 2.53 (broad s, 2 H).

1. temperatureThis was frozen with liquid nitrogen
2. customThe volatiles were removed by vacuum
3. customleaving a light brown, oily solid
4. extractionthe solution was extracted (4×50 ml) with methylene chloride
5. dry with materialThe organic layers were dried over sodium sulfate
6. customevaporated to dryness under vacuum to an oily brown solid (38%), which
7. additiona diastereomeric mixture of the desired products

ORD record

ord-729acff3d5bd49c6b22028a0627db1ef

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05955603