Silver Nitrate → 4-(Nitrooxy)butanoic acid

Temperature

60 °C

To a solution of 4-bromobutanoic acid [4-[[1-[[3, 5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]ester (150 mg, 0.22 mmol) in acetonitrile/THF (15 ml 2/1 v/v), AgNO3 was added (80 mg, 0.47 mmol) and the solution was heated in the dark at 60° C. for 6 hours. The silver salt was then filtered off (AgBr) and the solvent was evaporated at reduced pressure. The product thus obtained was purified by chromatography on silica gel with a mixture of ethyl acetate/hexane as eluent (4/6 v/v) to give 4-nitrooxybutanoic acid, [4-[[1-[[3,5-bis(1,1-dimethyletihyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis (1,1-dimethylethyl)-phenyl] ester (100 mg).

1. filtrationThe silver salt was then filtered off (AgBr)
2. customthe solvent was evaporated at reduced pressure
3. customThe product thus obtained
4. customwas purified by chromatography on silica gel with a mixture of ethyl acetate/hexane as eluent (4/6 v/v)

ORD record

ord-453ab883dde1411e8d154dfa0b604362

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166605B2