Water → Ethyl hydroxy-(2-isopropoxytetrahydro-3-furanyl)acetate

Participants

Reaction Steps

In a 1 L round button flask, titanium tetrachloride (17.83 mmoles; 1.96 mL; 3.38 g) was dissolved in dichloromethane (70 mL; 1.092 moles; 92.75 g) at room temperature. Then titanium tetra(isopropoxide) (17.83 mmoles; 5.28 mL; 5.07 g) dissolved in dichloromethane (70 mL; 1.092 moles; 92.75 g) was added dropwise at room temperature. After a 1 hour stirring period, ethyl glyoxalate (1.1 equiv; 39.24 mmoles; 3.55 mL; 4.0 g) free of toluene, dissolved in dichloromethane (8.75 mL; 136.5 mmoles; 11.59 g) was added dropwise over 30 min at room temperature. After 15 min., 2,3-dihydrofuran (2.5 g; 1.000 equiv; 35.67 mmoles; 2.70 mL) dissolved in dichloromethane (17.5 mL; 273.0 mmoles; 23.19 g) was added over 30 min. at room temperature. After a 3 hours stirring period, isopropyl alcohol (10 equiv; 356.7 mmoles; 27.26 mL; 21.44 g) was added dropwise. After 3 hours, the mixture of potassium carbonate (1.75 g; 12.66 mmoles) and diethanolamine (9.5 g; 90.6 mmoles) dissolved in water (175 mL; 9.72 moles; 175 g) was added to the reaction mixture. After stirring over a weekend, the two layers were separated and the organic layer was washed with (2×100 mL) of water (200 mL; 11.10 moles; 200.0 g). The organic solvent was evaporated over reduced pressure to afford the desired product (7.0 g; GC: 96 area %).

Provenance & Evidence