Hydrochloric Acid → HCID 68106974, compound

Triphenyl phosphine (7.87 g, 30 mmol) was dissolved in 80 mL of tetrahydrofuran followed by the addition of diethyl azodicarboxylate (5.23 g, 30 mmol) in a dry ice bath. The reaction mixture was stirred 30 minutes, added dropwise with a solution of methyl 3-hydroxy-4-nitro-benzoate 1b (2.96 g, 15 mmol) in tetrahydrofuran, and stirred 10 minutes followed by the addition of 2-methyl-allyl alcohol (1.41 g, 19.50 mmol), then stirred for another 1 hour. The resulting mixture was heated to room temperature and stirred for 12 hours. The resulting mixture was added with 10 mL of water, added dropwise with 1 M hydrochloric acid to adjust pH to 2 to 3 and extracted with ethyl acetate (50 mL×3). The combined organic phase was added dropwise with 1 M sodium hydroxide solution to adjust pH to 9 to 10, extracted with ethyl acetate (50 mL×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 3-(2-methylallyloxy)-4-nitro-benzoate 4a (3 g, yield: 79.6%) as a light yellow solid.

1. stirringstirred 10 minutes
2. stirringstirred for another 1 hour
3. stirringstirred for 12 hours
4. extractionextracted with ethyl acetate (50 mL×3)
5. additionThe combined organic phase was added dropwise with 1 M sodium hydroxide solution
6. extractionextracted with ethyl acetate (50 mL×2)
7. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-03202185c1254a4ea656b69031a33e22

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2