Hydrochloric Acid → HCID 15479558, compound

Participants

Reaction Steps

A solution of lithium hydroxide (84 mg, 2.0 mmol) in water (1.0 mL) is added to a solution of methyl ester 2 (455 mg, 0.6 mmol) in 1,4-dioxane (1.0 mL) at room temperature. The mixture is stirred at room temperature for 5 hours and a 1N solution of HCl (10 mL) is added. Dioxane is evaporated under reduced pressure and the mixture is diluted with EtOAc (20 mL). The separated aqueous layer is extracted with EtOAc (3×50 mL) and the combined organic layers are washed (brine), dried (MgSO4 anh.), filtered and evaporated. Flash-chromatography (HOAc:EtOH:EtOAc (0.1:1:9)) of the residue gives carboxylic acid 4 (210 mg, 48%). 1H NMR (CDCl3): δ 9.65 (1H, br. s), 7.98 (2H, d, J=8.1 Hz), 7.26 (20H, s), 7.13 (2H, d, J=8.1 Hz), 4.95 (8H, m), 3.31 (2H, td, J=16.7, 6.4 Hz), 2.82 (1H, tt, J=24.0, 6.4 Hz). 13C NMR (CDCl3): δ 170.0, 144.6 (t, J=7.6 Hz), 135.9, 135.8, 130.1, 129.0, 128.6, 128.5, 128.4, 128.3, 128.2, 128.1, 68.3 (dd, J=19.6, 6.5 Hz), 39.4 (t, J=133.2 Hz), 31.2 (br. s).

Provenance & Evidence