tert-butyl oxane-4-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetrahydro-2H-pyran-4-carboxylic acid (10 g, 77 mmol) and EDC (17.68 g, 92 mmol) were added to a flask, followed by DCM (200 ml). To the resulting suspension was added Et3N (16 ml, 115 mmol), tBuOH (16.1 ml, 169 mmol) and DMAP (9.39 g, 77 mmol). The reaction mixture was stirred at 40° C. for 18 hr. The reaction mixture was diluted with DCM (100 Ml) and washed with 1N NaOH (1×100 Ml) followed by 1M citric acid solution (1×100 Ml). The organic layer was dried over sodium sulfate, filtered and concentrated to afford tert-butyl tetrahydro-2H-pyran-4-carboxylate. 1H NMR (500 MHz, CDCl3) δ 3.90 (dt, 2H), 3.37 (dt, 2H), 2.38 (septet, 1H), 1.77-1.67 (m, 4H), 1.40 (s, 9H). washed with 1N NaOH (1×100 Ml) The organic layer was dried over sodium sulfate filtered concentrated