Triethylborane → Methyl 3-(3-ethyl-4-hydroxyphenyl)propanoate

Temperature

65 °C

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 3-(3-bromo-4-hydroxyphenyl)propanoate (220 mg, 0.85 mmol, 1.00 equiv), Pd(dppf)Cl2 (25.76 mg, 0.04 mmol, 0.04 equiv), Cs2CO3 (616.4 mg), tetrahydrofuran (5 mL), triethylborane (1.26 mL). The resulting solution was stirred overnight at 65° C. in an oil bath. The reaction was then quenched by the addition of 5 mL of water. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 20 mL of EA. The resulting mixture was washed with 3×10 mL of H2O. The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethylacetate/petroleum ether (10:90). This resulted in 300 mg (170%) of methyl 3-(3-ethyl-4-hydroxyphenyl)propanoate as colorless oil.

1. customInto a 50-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customThe reaction was then quenched by the addition of 5 mL of water
4. concentrationThe resulting mixture was concentrated under vacuum
5. additionThe resulting solution was diluted with 20 mL of EA
6. washThe resulting mixture was washed with 3×10 mL of H2O
7. dry with materialThe mixture was dried over anhydrous sodium sulfate
8. customThis resulted in 300 mg (170%) of methyl 3-(3-ethyl-4-hydroxyphenyl)propanoate as colorless oil

ORD record

ord-a5ce451417444c5caeb8f3921e094aef

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1