Ammonium Chloride → HCID 22006939, compound

Temperature

0 °C

A stirred solution of 8.0 grams (0.037 mole) of ethyl(2-ethylbenzoxazol-5-yl)carboxylate in 100 mL of anhydrous tetrahydrofuran was cooled to 0° C., and 20 mL (0.02 mole) of a 1.0 molar solution of lithium aluminum hydride in tetrahydrofuran was added portionwise from a syringe. Upon completion of the addition the reaction mixture was stirred at 0° C. for 15 minutes, then was allowed to warm to ambient temperature, where it stirred for about 18 hours. The reaction mixture was poured into a mixture of 250 mL of an aqueous solution saturated with ammonium chloride and ice. The mixture was then extracted with two 250 mL portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium chloride, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with ethyl acetate as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.1 grams of (2-ethylbenzoxazol-5-yl)methanol. The NMR spectrum was consistent with the proposed structure.

1. additionUpon completion of the addition the reaction mixture
2. temperatureto warm to ambient temperature
3. stirringwhere it stirred for about 18 hours
4. extractionThe mixture was then extracted with two 250 mL portions of diethyl ether
5. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
6. dry with materialdried with magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
9. concentrationconcentrated under reduced pressure

ORD record

ord-ba6783373e854882b9ad87f5725e9552

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05569664