Dimethylformamide → Methyl 6-formyl-1-naphthoate

Temperature

70 °C

Carbon monoxide (CO) gas was slowly bubbled through a solution of methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate (334 mg, 1.0 mmol), Pd(OAc)2 (22 mg, 0.10 mmol), 1,3-bis-(diphenylphosphino)propane (40 mg, 0.10 mmol) and triethylamine (0.28 mL, 2.0 mmol) an DMF (8.3 mL). After 15 min, trioctylsilane (0.90 mL, 2.0 mmol) was added as bubbling continued. The mixture was heated at 70° C., continuing to bubble CO into the solution. After 6 h at 70 the bubbling CO was replaced with a balloon of CO and the reaction mixture was stirred overnight. After 18 h at 70° C., the reaction was cooled to room temperature, diluted with EtOAc (150 mL) and washed with water (3×50 mL) and brine (50 mL). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 40 g silica gel (100% hexanes→25% EtOAc/hexanes, gradient) to afford 78 mg (36%) of methyl 6-formyl-1-naphthoate.

1. customas bubbling
2. customto bubble CO into the solution
3. waitAfter 6 h at 70 the bubbling CO was replaced with a balloon of CO
4. waitAfter 18 h at 70° C.
5. temperaturethe reaction was cooled to room temperature
6. additiondiluted with EtOAc (150 mL)
7. washwashed with water (3×50 mL) and brine (50 mL)
8. dry with materialThe organic phase was dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe resulting residue was purified on 40 g silica gel (100% hexanes→25% EtOAc/hexanes, gradient)

ORD record

ord-f1f9697f468c45b4bb16255818f39e02

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633220B2