Imidazole → (S)-methyl 4-(tert-butyldimethylsilyloxy)-3,4-dihydro-2H-chromene-7-carboxylate

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Reaction Steps

A mixture of (S)-methyl-4-hydroxyl-3,4-dihydro-2H-chromene-7-carboxylate (10.2 g, 49.0 mmol), imidazole (3.70 g, 53.9 mmol), and TBSCl (8.12 g, 53.9 mmol) in DMF (100 mL) was stirred for 24 h at RT. The reaction mixture was quenched with H2O and extracted with ether (3×). The organic extracts were dried over MgSO4, and concentrated to give a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.74 (s, 15H), 1.81 (m, 1H), 1.91 (m, 1H), 3.87 (s, 3H), 4.02 (m, 1H), 4.11 (m, 1H), 4.67 (t, 5.2 Hz, 1H), 7.09 (s, 1H), 7.11 (d, 7.6 Hz, 1H), 7.23 (d, 7.6 Hz, 1H).

Provenance & Evidence