2-Trimethylsilyloxyfuran

[61550-02-5] C7H12O2Si (MW 156.28) (provides 5-substituted 2(5H)-furanones by alkylation,2 aldolization,3 and conjugate addition;4 transforms quinones into furo[3,2-b]benzofurans;5 useful for the four-carbon elongation of sugars6) Alternate Names: TMSOF. Physical Data: bp 44–46 °C/17 mmHg; d 0.93 g mL−1. Solubility: sol most organic solvents, e.g. CH2Cl2, Et2O, benzene, THF, MeCN. Form Supplied in: colorless liquid; commercially available (98% pure) but expensive. Preparative Method: accessible by silylation of 2(5H)-furanone,1c,5b which is obtained at very low cost by oxidation of furfural (see also α,β‐Butenolide). Handling, Storage, and Precautions: flammable liquid; sensitive to moisture. To avoid hydrolysis, it should be kept under Ar at −18 °C or below. For best results, reactions should be performed under strictly anhydrous conditions in aprotic solvents. Use in a fume hood.