Fluorene → HCID 22407026, compound

A solution of fluorene (5.04 g; 30.32 mmol) in THF (50 mL) was cooled to 0° C. and treated with n-butyllithium (12.13 mL of a 2.5M solution in hexanes; 30.32 mL). After stirring the resulting dark red mixture for 20 minutes, a solution of 2-(2-bromoethyl)-1,3-dioxolane (6.03 g; 33.35 mmol) in 20 mL of THF was added, and the resulting mixture was stirred overnight, allowing it to come to room temperature. It was quenched by the addition of saturated ammonium chloride (50 mL) and extracted into ethyl acetate (50 mL). The organic phase was washed with brine, dried and freed of solvent. The crude residue was purified on a flash chromatography column, eluting with 20% ethyl acetate in hexane, to obtain 5.74 g (72%) of the product as an oil. 1H NMR (CDCl3): δ 1.43 (m, 2H); 2.18 (m, 2H); 3.82, 3.86 (m, 2H each); 4.15 (t, 1H); 4.77 (t, 1H); 7.31 (m, 4H); 7.51 (dd, 2H); 7.68 (dd, 2H).

1. stirringthe resulting mixture was stirred overnight
2. customto come to room temperature
3. customIt was quenched by the addition of saturated ammonium chloride (50 mL)
4. extractionextracted into ethyl acetate (50 mL)
5. washThe organic phase was washed with brine
6. customdried
7. customThe crude residue was purified on a flash chromatography column
8. washeluting with 20% ethyl acetate in hexane

ORD record

ord-34cc122515f94588861f203f174c09fb

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05519043