Acetic Acid → HCID 57421777, compound

Temperature

0 °C

Diisopropylamine (0.55 mL, 3.9 mmol) was dissolved in dry tetrahydrofuran (10 mL), and 2.66 M n-butyllithium in hexane (1.4 mL, 3.6 mmol) was added dropwise at 0° C. The reaction solution was stirred at 0° C. for 10 minutes and cooled to −78° C., and after dropwise addition of tert-butyl acetate (0.58 mL, 4.3 mmol), stirred at −78° C. for 30 minutes. Methyl 4-formylbenzoate (0.70 g, 4.3 mmol) in tetrahydrofuran (6 mL) was added dropwise at −78° C. over 5 minutes, and the reaction solution was stirred at −78° C. for 10 minutes and at 0° C. for 1 hour, then adjusted to pH 7 with acetic acid (0.43 mL, 7.5 mmol) and returned to room temperature over 12 hours. The solution was concentrated by evaporating tetrahydrofuran under reduced pressure, and ethyl acetate and water were added. The organic layer was separated and dried under reduced pressure to dryness to give 1.17 g of the crude desired product. The crude desired product was purified by silica gel column chromatography (Merck silica gel 60, 22 g, n-hexane-ethyl acetate 4:1) to give 0.84 g of the desired product (yield 84%).

1. temperaturecooled to −78° C.
2. stirringstirred at −78° C. for 30 minutes
3. stirringthe reaction solution was stirred at −78° C. for 10 minutes and at 0° C. for 1 hour
4. waitreturned to room temperature over 12 hours
5. concentrationThe solution was concentrated
6. customby evaporating tetrahydrofuran under reduced pressure, and ethyl acetate and water
7. additionwere added
8. customThe organic layer was separated
9. customdried under reduced pressure to dryness
10. customto give 1.17 g of the crude desired product
11. customThe crude desired product was purified by silica gel column chromatography (Merck silica gel 60, 22 g, n-hexane-ethyl acetate 4:1)

ORD record

ord-574f27a3fbc74b31a65db824f0b04206

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134013B2