HCID 3423433, compound → HCID 15058655, compound

A solution of 3.0 grams (0.015 mole) of 4-acetamidophenyl 2-fluoroethyl ether in 15 ml of dry tetrahydrofuran was added dropwise to a stirred solution of 15 ml of a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al®) in toluene and 50 ml of dry tetrahydrofuran. The reaction mixture was stirred at room temperature for approximately 18 hours. The mixture was quenched with 1 ml of water and was filtered. The filtrate was evaporated under reduced pressure leaving a dark liquid which solidified upon standing. This solid was dissolved in ethyl acetate to which a small amount of water was added. A small amount of precipitate formed from which the organic solution was decanted. The organic solution was evaporated under reduced pressure leaving a dark liquid residue. This residue was purified by column chromatography on silica gel followed by distillation under reduced pressure to yield 1.6 grams of 4-(ethylamino)phenyl 2-fluoroethyl ether as a solid.

1. customThe mixture was quenched with 1 ml of water
2. filtrationwas filtered
3. customThe filtrate was evaporated under reduced pressure
4. customleaving a dark liquid which
5. additionwas added
6. customA small amount of precipitate formed from which the organic solution
7. customwas decanted
8. customThe organic solution was evaporated under reduced pressure
9. customleaving a dark liquid residue
10. customThis residue was purified by column chromatography on silica gel
11. distillationfollowed by distillation under reduced pressure

ORD record

ord-91d889fc7be549e59c8435d2a94b999f

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960884