Methyl chloroacetate → Methyl 2-(2-methylfur-5-ylthio)acetate

Participants

Reaction Steps

The necessary starting material was prepared from 2-methylfuran (16.4 g) by an analogous procedure to that described for furan itself in Example 14, except that in this case the intermediate lithium salt of 2-methylfuran-5-thiol was reacted in dry ether at -20° C. with methyl 2-chloroacetate. The reaction mixture was stirred for 2 days and then partitioned between water (800 ml) and ether (3×400 ml). The organic layers were dried (MgSO4) and evaporated. The residual oil was distilled to give methyl 2-(2-methylfur-5-ylthio)acetate (40.1 g) b.p. 94°-96° C./0.5 mm; NMR (90 MHz): 2.30 (s,3H), 3.45 (s,2H), 3.70 (s,3H), 5.95 (m,1H), 6.45 (d,1H).

Provenance & Evidence