Acetic Acid → HCID 59132625, compound

Participants

Reaction Steps

Condensation with Meldrum's acid is carried out according to the procedure of DeWolf et al. (1989) Biochemistry 28: 3833-3842. A solution of Meldrum's acid (18 g, 124 mmol) compound 12.1 (30 g, 124 mmol) in toluene (100 mL) was treated with glacial acetic acid (4 mL) and piperidine (2 mL). The reaction mixture was stirred and heated at reflux until the removal of water with a Dean-Stark trap was complete. The reaction mixture was cooled to room temperature and the resulting solid was filtered and washed with cold toluene to yield 28 g (62%) of 12.2 as a bright yellow powder. 1H NMR (400 MHz)(DMSO-d6) δ 8.32 (s, 1H); 8.24 (d, 2H, J=8.9 Hz); 7.42 (d, 2H, J=8.6 Hz); 7.17 (d, 2H, J=9.0 Hz); 6.97 (d, 2H, J=8.7 Hz); 5.18 (s, 2H) 3.75 (s, 6H) 1.75 (s, 6H).

Provenance & Evidence