Estrone → (+)-Estrone 3-methyl ether

Participants

Reaction Steps

Estrone (1, 100.0 g, 370 mmol) was dissolved in MeOH (1.5 L), followed by the addition of K2CO3 (300.0 g, 2.17 mol). MeI (310 mL, 4.98 mol) was added and the mixture stirred at room temperature for 70 h. The reaction mixture was concentrated in vacuo to remove some of the MeOH and was then poured into ice water forming a precipitate. The solid was collected and dried by partitioning into CH2Cl2. The organic layer was dried over MgSO4, and the solvent was removed in vacuo to yield compound 2 (105.0 g) as white crystals in quantitative yield. 1H NMR (250 MHz, CDCl3); δ 0.91 (s, 3, C-18 H), 3.78 (s, 3, MeO), 6.65 (s, 1, C-4 H), 6.72 (d, 1, J=8.57 Hz, C-2 H), 7.21 (d, 1, J=8.57 Hz, C-1 H).

Provenance & Evidence