Tetrahydrofuran → Methoxyindoline

To an ice-cold solution of indoline 9 (377 mg, 1.6 mmol) dissolved in tetrahydrofuran (5 mL) and kept under an argon atmosphere was added lithium triethylborohydride (3.2 mL, 3.2 mmol), and the mixture was stirred over the range of 0° C. to room temperature for 20 h. The reaction mixture was quenched with 3N hydrochloric acid, and volatiles were removed under vacuum. The resulting solution was acidified to pH 2 with additional 3N hydrochloric acid and washed with methylene chloride. The aqueous solution was basified with saturated aq. sodium bicarbonate and extracted with methylene chloride. The organic extracts were washed with brine and dried (MgSO4). Removal of solvents gave crude methoxyindoline (200 mg, 65% yield) as a brownish yellow oil, which was used without further purification.

1. customThe reaction mixture was quenched with 3N hydrochloric acid, and volatiles
2. customwere removed under vacuum
3. washwashed with methylene chloride
4. extractionextracted with methylene chloride
5. washThe organic extracts were washed with brine
6. dry with materialdried (MgSO4)
7. customRemoval of solvents

ORD record

ord-c308900fe55340dd8bb9eec128e4c616

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05674876