Sodium Thiosulfate → 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)butanal

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butan-1-ol (5.0 g, 24 mmol) in CH2Cl2 (80 mL) was added Dess-Martin periodinane reagent (10 g, 24 mmol). The reaction mixture was subsequently stirred for 20 hours at 25° C. The solution was diluted with Et2O (200 mL) and a 1:1 mixture of 10% sodium thiosulfate and saturated NaHCO3 (200 mL) was added. The mixture was stirred rapidly for 10 min until both phases were clear. The layers were separated and the aqueous phase was extracted with Et2O (100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to 50% of its original volume to give 4,4,4-trifluoro-2-(2,2,2-trifluoro-ethyl)-butyraldehyde that was used as is for the subsequent reaction.

Provenance & Evidence