Acetic Acid → HCID 11796064, compound

Temperature

11 °C

A solution of chromium trioxide (5.14 g, 51.4 mmol) in 90% glacial acetic acid (50 ml) was added dropwise at 10-12° C. to a mechanically-stirred solution of 4 (4.82 g, 12.03 mmol) in glacial acetic acid (77 ml). After the addition, the resulting mixture was stirred at 10-12° C. for 40 min. The mixture was poured into ice-water mixture (400 ml) and the compounds were extracted with ethyl acetate (300, 200, and 100 ml). The organic layers were washed with brine (2×200 ml), solution of sodium bicarbonate (2×150 ml) and brine (2×200 ml), dried over sodium sulfate and evaporated to dryness. Chromatography of the residue on a silica gel column using 30% ethyl acetate in hexane gave the title compound 5 (3.9 g, 78%), which was crystallized from ethyl acetate/hexane to afford white crystals: mp 193-194° C. (lit.12 mp 195° C.); IR (KBr) 1774, 1736, 1719 (C═O); 1H NMR (CDCl3) δ7.75 (s, 1 H), 6.95 (s, 1 H), 4.75 (t, J=8.5 Hz, 1 H), 4.19 (q, J=6.9 Hz, 2 H), 2.85-2.48 (m, 2 H), 2.45-1.1 (m, 19 H), 0.85 (s, 3 H).

1. additionAfter the addition
2. extractionthe compounds were extracted with ethyl acetate (300, 200, and 100 ml)
3. washThe organic layers were washed with brine (2×200 ml), solution of sodium bicarbonate (2×150 ml) and brine (2×200 ml)
4. dry with materialdried over sodium sulfate
5. customevaporated to dryness

ORD record

ord-1ed675bfede549c9a9985ab712ef2b80

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696436B1