Water → 7,9-Dimethoxy-5-oxa-11-thia-benzo[b]fluoren-10-one

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Reaction Steps

A solution consisting of methyl thiosalicylate 28 (0.67 g, 4.0 mmol) in DMF was treated with NaH (0.19 g, 4.8 mmol as a 60% dispersion in mineral oil) and stirred at rt for approximately 5-10 minutes and then Example 27 (1 g, 4.3 mmol) was added followed by additional NaH (0.4 g, 10 mmol, as a 60% dispersion in mineral oil) and the reaction was heated at 100° C. for 30 minutes. The crude reaction mixture was poured into water, filtered, and the solid product washed with additional water, MeOH and hexanes. The product thus obtained was triturated with MeOH to yield 29 (0.51 g): 1H NMR (DMSO-d6) δ 8.16 (d, 2H, J=2.3 Hz), 7.71-7.61 (m, 2H), 6.91 (d, 1H, J=2.3 Hz), 6.63 (d, 1H, J=2.3 Hz), 3.95 (s, 3H), 3.89 (s, 3H); MS 335 (M+Na)+.

Provenance & Evidence