Acetic Anhydride → HCID 12113351, compound

To a 250 mL round bottom flask were added 2-methoxybenzaldehyde (2.0 g, 14.7 mmol), diethyl butanedioate (6.4 g, 36.7 mmol) and t-BuOH (35 mL). KO-t-Bu (3.3 g, 29.4 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 hours and then diluted with 0.5 N HCl (120 mL) and extracted with EtOAc. The organic layer was back extracted with 5% KOH (60 mL). Aqueous layer was acidified with 1N HCl and extracted with EtOAc. Organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was treated with Ac2O (9.7 mL, 103 mmol) and NaOAc (2.05 g, 25 mmol) at 120° C. under nitrogen overnight. The reaction mixture was cooled with an ice bath and diluted with 150 mL of water. The aqueous solution was carefully removed by slow decantation. The remaining residue was dissolved in EtOAc (30 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified on a silica gel column eluting with a gradient of 100% hexanes to 25% EtOAc/hexanes to give the title intermediate (0.52 g) as a light yellow solid.

1. extractionextracted with EtOAc
2. extractionThe organic layer was back extracted with 5% KOH (60 mL)
3. extractionextracted with EtOAc
4. washOrganic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. temperatureThe reaction mixture was cooled with an ice bath
9. customThe aqueous solution was carefully removed by slow decantation
10. dissolutionThe remaining residue was dissolved in EtOAc (30 mL)
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated
14. customThe crude product was purified on a silica gel column
15. washeluting with a gradient of 100% hexanes to 25% EtOAc/hexanes

ORD record

ord-aa1f0a089b834e99a2f8e5ae7d847c9b

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2