Sodium Hydroxide → HCID 70569336, compound

Participants

Reaction Steps

To a suspension of copper iodide (10.49 g, 57.3 mmol) in dry tetrahydrofuran (50 ml) and diethyl ether (50 ml), cooled in an ice bath, methyl lithium (60 ml of a 1.84 molar solution, 0.11 mol) was added under a nitrogen atmosphere. After 10 minutes, a solution of 14-methoxycodeinone (14) (15.0 g, 45.8 mmol) in tetrahydrofuran (300 ml) was added and the mixture was stirred for another 3 hours. At the end of this period, a saturated solution of ammonium chloride (200 ml) was added slowly. This was followed by the addition of a 20% NaOH solution until the mixture was basic. The aqueous layer was separated and extracted with ethyl acetate (3×100 ml) whereupon the organic extracts were combined, washed once with water (100 ml), dried over MgSO4, filtered and evaporated to give crude (20). This material was recrystallized from ethanol to give 8 g (51% theory) of the title compound as a colorless solid, m.p. 204°-205° C.

Provenance & Evidence