Diisopropylethylamine → HCID 136378615, compound

Participants

Reaction Steps

To (E)-methyl 6-(4-hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)hept-2-enoate (VII; 0.63 g, 2.05 mmol) in 30 ml anhydrous CH2Cl2 at −72° C., was added titanium tetrachloride (0.88 ml; 8 mmol; Aldrich) under argon, and the reaction mixture was stirred for 20 min. DIPEA (1.64 ml; 9.43 mmol; Aldrich) was added, and the reaction mixture was stirred for 90 min. (E)-3-methyl-octenal (XXI; 1 g; 7.25 mmol) in 5 ml anhydrous CH2Cl2 was added in two portions over 10 min, and the reaction mixture was stirred at −72° C. for 48 h and at 0° C. for 1 hour. The reaction was quenched with 40 ml ice water and extracted with 2×40 ml CH2Cl2. The CH2Cl2 extracts were pooled, washed with saturated NH4Cl, washed twice with saturated NaHCO3, and dried with anhydrous Na2SO4. The product was purified by silica flash chromatography (EtOAc gradient in hexanes).

Provenance & Evidence