Triacetoxyperiodinane → 4-Methyloxane-4-carbaldehyde

Participants

Reaction Steps

To a solution of (4-methyl-tetrahydro-pyran-4-yl)-methanol (1.5 g, 11.5 mmol) in CH2Cl2 was added a suspension of Dess-Martin periodinane (5.8 g, 14 mmol) in CH2Cl2 (30 mL). After 70 min, the heterogenous mixture was diluted with Et2O (100 mL), stirred for 10 min, treated with 1 N HaOH (10 mL), and stirred for another 10 min. The mixture was filtered, and the filtrate was concentrated. The residue was purified by chromatography (Et2O/CH2Cl2) to give the title compound (1.01 g, 68%) as a colorless volatile oil. The spectral data matched that reported in PCT Intl. Pat. Appl. Publ. No. WO 2006/001752.

Provenance & Evidence