Citric Acid → HCID 58687939, compound

Participants

Reaction Steps

To a solution of the compound from Step E above (2.68 g, 3.41 mmol) in tetrahydrofuran (50 mL) at −78° C. was added 2.0M phenyllithium in cyclohexane (1.70 mL, 3.41 mmol). After the reaction was stirred for 5 min, 10% citric acid in THF was added. The mixture was diluted with ethyl ether, washed sequentially with water and saturated brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (silica gel; 10 to 15% ethyl acetate/hexanes gradient elution) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 4.74 (s, 2H), 4.08 (s, 3H), 0.99 (s, 9H), 0.17 (s, 6H). LC/MS: 400/402 (M+H and M+H+2).

Provenance & Evidence