Hydrochloric Acid → [4-(Pyrid-2-yloxy)phenyl]methanol

Under an atmosphere of argon, 4-(2-pyridyloxy)benzoic acid (1.08 g, 5.02 mmol) was dissolved in 20 mL of dehydrated tetrahydrofuran. Under cooling with ice and stirring, 1 mol/L borane-tetrahydrofuran complex (15.1 mL, 15.1 mmol) was added dropwise for 5 minutes and the mixture was allowed to stand overnight at room temperature. Under cooling with ice, 2 mL of 6 mol/L hydrochloric acid were added dropwise and, after stirring for 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue was poured into 100 mL of ice water and, after salt was saturated, the mixture was made alkaline with potassium carbonate, which was extracted with ethyl acetate. The extracted solution was dried over anhydrous sodium sulfate and then concentrated to obtain 1.01 g (100%) of the title compound as a pale yellow oil.

1. temperatureUnder cooling with ice
2. addition1 mol/L borane-tetrahydrofuran complex (15.1 mL, 15.1 mmol) was added dropwise for 5 minutes
3. additionwere added dropwise
4. stirringafter stirring for 30 minutes
5. concentrationthe reaction mixture was concentrated under reduced pressure
6. additionThe residue was poured into 100 mL of ice water
7. extractionwas extracted with ethyl acetate
8. dry with materialThe extracted solution was dried over anhydrous sodium sulfate
9. concentrationconcentrated

ORD record

ord-4714ae4408cd4836b9c619da762c59f1

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176204B2