Tetrahydrofuran → HCID 22457346, compound

Participants

Reaction Conditions

Reaction Steps

4-Vinylphenylacetic acid 34 (8.15 g, 50.3 mmol) was placed in a three-neck round bottom flask attached with a thermometer, and an addition funnel with a drying tube. Tetrahydrofuran (80 mL, distilled over Na/K alloy) was added to the reaction flask, and the solution was cooled with an ice bath. Trifluoroacetic anhydride (15 mL, 106.2 mmol) was slowly added using an addition funnel so that the reaction temperature was kept below 10° C. The solution was allowed to stir at 5° C. for 2 h. A solution of 2-Methylpropanol (freshly distilled over CaH2, 36 mL, 376 mmol) in THF (50 mL) was added dropwise keeping the reaction temperature below 10° C. The solution was stirred for an additional 2 hours at 5° C., and then overnight at room temperature. Ethyl ether (200 mL) was added to the solution, and 170 mL of 1.25 N aqueous NaOH was slowly added while cooling with an ice bath. The solution was then allowed to stir at room temperature for 2 h. The organic layer was separated, washed with water until neutral, washed with brine, and then dried over anhydrous MgSO4. The solvents were removed in vacuo, and 9.85 g of clear liquid was obtained in 90% yield.

Provenance & Evidence