Diethyl Ether → HCID 13471169, compound

Participants

Reaction Steps

A mixture of Compound VI (5 g, 13 mmoles) and dry, technical-grade silver fluoride (5 g, 22.1 mmoles) in dry pyridine (90 ml) was stirred for 14 hours at 25° C, after which time, t.l.c. (2:3 benzene-acetone) showed that all of Compound VI had reacted. The dark solution was poured into ether (500 ml), and the resultant mixture was filtered. The filtrate was evaporated at ≤40° C, and then three 25-ml portions of toluene were added to and evaporated from the residue (to remove all of the pyridine). The resultant syrup was taken up in ether, and the suspension filtered through a small column (250 × 20 mm) of silica get to remove residual silver salts. The effluent was evaporated in vacuo to give the pure Compound VII as a syrup; yield 4 g (100%), [α]D23 +55.2° (c, 1.4, chloroform); νmaxfilm 3420-3290 (NH), 1725 (ester CO), 1660 (Amide I, C=C), 1600, 1585 (monosubstituted phenyl), and 1525 cm-1 (Amide II).

Provenance & Evidence