1-Pentanol → HCID 58896775, compound

A solution of pentanol (2.7 g, 31 mmol) and tert-butoxide (3.5 g, 31 mmol) in solvent of tert-butanol was stirred for 1 hr at room temperature followed by addition of 4-nitropyridine-N-oxide (4 g, 28.6 mmol). After the reaction was done, the resulting solution was worked up with ethyl acetate and water, separated and the organic solvent was dried completely. After the addition of toluene, the solvent was removed under a reduced pressure. Acetic anhydride (40 ml) was added to the residual mixture and refluxed for 3 hrs. Acetic anhydride was dried completely followed by adding of MeOH (20 ml) and 3N NaOH (5 ml) and stirring 1 hr. MeOH was dried adequately then the residual mixture was made neutral with 6N HCl. The resulting solution was extracted with Ethyl acetate (80 ml) and subjected to silica gel column chromatography (ethyl acetate/MeOH, 10:1) to obtain the titled compound (2.3 g, 56%).

1. customseparated
2. customthe organic solvent was dried completely
3. additionAfter the addition of toluene
4. customthe solvent was removed under a reduced pressure
5. additionAcetic anhydride (40 ml) was added to the residual mixture
6. temperaturerefluxed for 3 hrs
7. dry with materialAcetic anhydride was dried completely
8. additionby adding of MeOH (20 ml) and 3N NaOH (5 ml)
9. dry with materialMeOH was dried adequately
10. extractionThe resulting solution was extracted with Ethyl acetate (80 ml)

ORD record

ord-a6aedd9f5aa449cd83a17b3052e01d96

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973060B2