tert-Butanol → 3-Oxo-3-(tetrahydro-pyran-4-yl)-propionic Acid Tert-butyl Ester

Participants

Reaction Steps

tert-Butanol (600 ul, 6 mmol) was added to a solution of 2,2-dimethyl-5-(tetrahydro-pyran-4-carbonyl)-[1,3]dioxane-4,6-dione (1.1 g, 4 mmol) in toluene (9.6 ml). The reaction mixture was heated under reflux conditions for 6 h and partitioned between ice water/brine 1/1 and iPrOAc. The layers were separated and the aqueous layer was extracted one more time with iPrOAc. The combined extracts were washed with ice water/brine 1/1, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give the title compound (891 mg, 3.9 mmol; 91%) as brown oil which was sufficiently pure to be used in the next reaction step. MS (EI): m/z=228 [M]+.

Provenance & Evidence