Methanol → HCID 59636036, compound

Participants

Reaction Steps

Example 13 (1.18 g, 3.0 mmol) in THF (10 mL) was added drop wise over 10 min to a solution of carbonyldiimidazole (1.5 g, 9.25 mmol) in THF (10 mL). The mixture was stirred for 30 min. Next, MeOH (20 mL) was added followed by the addition of NaOMe (0.162 g, 3 mmol). The reaction mixture was stirred for 5 min and then concentrated in vacuo. To the residue was added EtOAc and washed twice with 1M HCl and once with sat. NaHCO3 aq. The organic layer was dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel chromatography on a 120 g ISCO column eluting with a gradient from 100% CH2Cl2 up to 6% MeOH/CH2Cl2. The product was collected, concentrated in vacuo, and dried to give 1.2 g of Example 14.

Provenance & Evidence