Methyl chloroformate → Methyl 2-(4-cyanonaphthalen-1-yl)acetate

Temperature

0 °C

To a solution of 4-methyl-1-cyanonaphthalene (4.35 g, 25.9 mmol) in THF (100 mL) was cooled to −78° C. and treated with commercially available LDA (2 M, 60 mL). The reaction mixture was then warmed to 0° C. and maintained at 0° C. for 30 min. The resulting red-colored solution was cooled to −78° C. and methyl chloroformate (10 mL, 130 mmol) was added. The reaction mixture was stirred while warming to rt until the displacement was complete (4 h) and then quenched with sat'd NH4Cl. The THF layer was evaporated and extracted with EtOAc (3×20 mL). The EtOAc was dried over Na2SO4 and concentrated in vacuo to afford an oil.

1. temperaturemaintained at 0° C. for 30 min
2. temperatureThe resulting red-colored solution was cooled to −78° C.
3. temperaturewhile warming to rt until the displacement
4. custom(4 h)
5. customquenched with sat'd NH4Cl
6. customThe THF layer was evaporated
7. extractionextracted with EtOAc (3×20 mL)
8. dry with materialThe EtOAc was dried over Na2SO4
9. concentrationconcentrated in vacuo
10. customto afford an oil

ORD record

ord-fcac02bdec0b40e194a5e595e8dc174e

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07388027B2