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

Temperature

25 °C

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.

1. additionwas added
2. stirringThe mixture was stirred rapidly for 10 min until both phases
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with Et2O (100 mL)
5. washThe combined organic layers were washed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to 50% of its original volume

ORD record

ord-acdfe1ab9df34db2ad940eef9f113472

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550629B2