Boron tribromide → Ethyl 2-(5-hydroxy-2,3-dihydro-1h-inden-1-yl)acetate

Temperature

30 °C

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 2-(5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate (200 mg, 0.85 mmol, 1.00 equiv), dichloromethane (5 mL). This was followed by the addition of BBr3 (1 mL) at −78° C. The resulting solution was stirred for 15 min at 30° C. The reaction was then quenched by the addition of 5 mL of water/ice. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (30:70). This resulted in 150 mg (74%) of ethyl 2-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil.

1. customInto a 100-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customThe reaction was then quenched by the addition of 5 mL of water/ice
4. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationThe resulting mixture was concentrated under vacuum
7. customThis resulted in 150 mg (74%) of ethyl 2-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil

ORD record

ord-0926d3f8f1604cceb3361b544596ade4

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1