Sodium Thiosulfate → 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanal

Participants

Reaction Steps

To a suspension of 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol (1.16 g, 6.68 mmol) in dichloromethane (20 ml) at 0° C. was added portionwise Dess-Martin periodinane (3.26 g, 7.68 mmol), and the reaction mixture was stirred at the same temperature for 20 minutes, followed by addition of saturated aqueous NaHCO3 and Na2S2O3. The resulting mixture was stirred for 3 hours and the reaction mixture was extracted with Et2O. The combined organic phases were dried and concentrated in vacuo to give 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanal (958 mg, 5.56 mmol, 83% yield) as a colorless oil which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (s, 3H) 1.23 (s, 3 H) 1.33-1.85 (m, 6H) 3.32-3.44 (m, 1H) 3.73-3.89 (m, 1H) 4.61-4.70 (m, 1H) 9.44 (s, 1 H).

Provenance & Evidence