Acetic Acid → HCID 54682298, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.3 mL of diisopropylamine (23.5 mmol) in dry THF (500 mL) was cooled to 0° C. under nitrogen, treated with 14.3 mL of 1.64M n-butyllithium (22.8 mmol), and stirred at 0° C. for 25 minutes. To this solution was added 1.2 mL (11.1 mmol) of methyl acetoacetate, and the mixture was stirred for 30 minutes. The solution was then cooled to -78° C. A solution of 5.00 g (11.1 mmol) of 1,5-bis-(3-benzyloxy-phenyl)-pentan-3-one (prepared in Example J) dissolved in dry THF (100 mL) was added dropwise, and the mixture was stirred at low temperature for 3 hours. Dilute acetic acid (2 equivalents) was added, and the mixture was extracted with EtOAc. The extracts were dried (MgSO4) and concentrated. The residue that was obtained was dissolved in THF (250 mL), treated with 0.1N NaOH (500 mL), and stirred overnight at room temperature. The mixture was cooled in an ice bath, quenched with 50% acetic acid, and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel, eluting with MeOH:CH2Cl2 (2:98), to give 6,6-bis-[2-(3-benzyloxy-phenyl)-ethyl]-5,6-dihydro-4-hydroxy-pyran-2-one. 1H NMR (DMSO-d6) δ 1.93 (m, 4 H), 2.56 (m, 4 H), 3.35 (s, partially obscured by H2O, 2 H), 4.99 (s, 1 H), 5.02 (s, 4 H), 6.72-6.78 (m, 4 H), 6.82 (br s, 2 H), 7.14 (t, 2 H), 7.26-7.39 (m, 10 H).

Provenance & Evidence