Water → 5-Chloro-3-methyl-1-benzofuran-2-carbaldehyde

To a solution (40 mL) of 5-chloro-N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide (2.15 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (322 mg) at 0° C., and the mixture was stirred for 1 hr. Water (320 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (320 μL) was added, and the mixture was stirred at room temperature for 1 hr. The resulting insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (tetrahydrofuran) to give a pale-yellow solid. The obtained solid was washed with diisopropyl ether to give the title object compound (1.21 g, 73%) as a pale-yellow solid.

1. customto quench
2. customthe reaction, 1N aqueous sodium hydroxide solution (320 μL)
3. additionwas added
4. stirringthe mixture was stirred at room temperature for 1 hr
5. filtrationThe resulting insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (tetrahydrofuran)
8. customto give a pale-yellow solid
9. washThe obtained solid was washed with diisopropyl ether

ORD record

ord-c22ba26ca66f4669833c082c24c6db14

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2