Ethyl Acetate → HCID 16731847, compound

Participants

Reaction Steps

To 71C (2.00 g, 4.47 mmol) in THF (45 mL) was added a 1 M THF solution of TBAF (4.47 mL, 4.47 mmol). After stirring at rt for 45 min, saturated aqueous ammonium chloride and EtOAc were added and the layers were separated. The organic layer was washed with brine then dried (MgSO4), filtered and concentrated. The resulting residue was purified via flash chromatography eluting with 75-100% EtOAc/hexane to provide the title compound (1.36 g) which contained a minor impurity (6.76%). To obtain an analytically pure sample, a portion of the product (ca. 250 mg) was purified via preparative HPLC (YMC ODS C-18, 30×100 mm, eluting with 25% solvent B (solvent B=10% H2O-90% CH3CN-0.1% TFA) for 25 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide, after recrystallization from MeOH/water, the title compound (106 mg) as white needles. MS: m/z 665 [2M−H]−

Provenance & Evidence