Borane → Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

Temperature

0 °C

To a stirred solution of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (2.66 g, 8.89 mmol) in dry tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added 1 M of borane solution in tetrahydrofuran (20 mL, 20 mmol). The reaction was stirred at 0° C. for 30 minutes after the addition was complete, and then the cooling bath was removed. After being stirred for 2 hours at room temperature, the reaction mixture was cooled at 0° C. and quenched by addition of 2 M aq. HCl (30 mL). The mixture was stirred for 1 hour at room temperature, and then extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

1. additionafter the addition
2. customthe cooling bath was removed
3. stirringAfter being stirred for 2 hours at room temperature
4. temperaturethe reaction mixture was cooled at 0° C.
5. customquenched by addition of 2 M aq. HCl (30 mL)
6. stirringThe mixture was stirred for 1 hour at room temperature
7. extractionextracted with EtOAc (50 mL×3)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over anhydrous MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by silica gel column

ORD record

ord-423d5fa623ce4df7b5720b5c278a8f8c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946439B2