Acetic Anhydride → HCID 19106822, compound

Participants

Reaction Conditions

Reaction Steps

To 20.0 mL of tetramethyldiaminomethane was added 10.0 g of 6,7-dihydrobenzo[b]thiophen-4(5H)-one all at once. To this mixture was added 20.0 mL of acetic anhydride, dropwise. The reaction mixture exothermed to 45° C. and was heated to 122° C. for 15 minutes and then cooled to 90° C. where it was kept for 60 minutes. The dark solution was poured into cold water and extracted with ether. The ether was extracted with a saturated solution of NaHCO3 and then washed with brine. The ether layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The yellow oil was flash-chromatographed using 10% ethyl acetate and 90% hexanes as eluent to afford 6.18 g of a white solid, m.p. 47°-49° C. 200 MHz1H NMR(CDCl3) δ2.97 (t, 2H), 3.07 (t, 2H), 5.46 (s, 1H), 6.17 (s,1H), 7.11 (d, 1H), 7.48 (d, 1H); I. R. (Nugol) 1660 cm-1.

Provenance & Evidence