Ammonium Chloride → 1-Methylidene-2,3-dihydro-1H-inden-4-ol

To a suspension of CH3PPh3I (924 mg, 2.29 mmol) in Et2O (20 mL) was added t-BuOK (256 mg, 2.29 mmol). The mixture was stirred for 15 minutes, to which was added dropwise 4-(tert-butyl-dimethyl-silanyloxy)-indan-1-one (500 mg, 1.91 mmol). The mixture was stirred at room temperature overnight and then diluted with diethylether. The mixture was filtered on a pad of celite. The remaining precipitate was washed with diethylether. The combined filtrate was concentrated under reduced pressure. The crude compound was dissolved in THF and then was added 1M-TBAF (in THF, 1.2 eq). The reaction mixture was stirred for 30 min at room temperature, treated with saturated ammonium chloride, and then extracted with EtOAc. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography to give 1-methylene-indan-4-ol (200 g, 72%).

1. stirringThe mixture was stirred at room temperature overnight
2. filtrationThe mixture was filtered on a pad of celite
3. washThe remaining precipitate was washed with diethylether
4. concentrationThe combined filtrate was concentrated under reduced pressure
5. dissolutionThe crude compound was dissolved in THF
6. stirringThe reaction mixture was stirred for 30 min at room temperature
7. extractionextracted with EtOAc
8. dry with materialThe organic layer was dried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by column chromatography

ORD record

ord-a0f80dc04c8c4bb69fd1d89f7297ee99

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691855B2