Triethylsilane → 4-Chloroindoline

Temperature

50 °C

4-Chloroindole (3.15 g) was dissolved in trifluoroacetic acid (32 ml), thereto was added triethylsilane (8.3 ml) and the mixture was heated at 50° C. with stirring for 30 minutes. The resultant mixture was cooled to room temperature, and trifluoroacetic acid was evaporated under reduced pressure. To the residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate twice. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to give 4-chloro-2,3-dihydro-(1H)-indole (2.89 g) as colorless oil. APCI-Mass m/z 154/156 (M+H)

1. customtrifluoroacetic acid was evaporated under reduced pressure
2. additionTo the residue was added a saturated aqueous sodium hydrogen carbonate solution
3. extractionthe mixture was extracted with ethyl acetate twice
4. dry with materialThe organic layer was dried over magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)

ORD record

ord-482ce27b9b7a498a88960207b8990ca1

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2