[4-(PYRID-2-YLOXY)PHENYL]METHANOL synthesis

7synthesis methods

Product Name:[4-(PYRID-2-YLOXY)PHENYL]METHANOL
CAS Number:194017-70-4
Molecular formula:C12H11NO2
Molecular Weight:201.22

51363-00-9 Synthesis

51363-00-9
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Yield:194017-70-4 100%

Reaction Conditions:

Stage #1: 4-(pyridin-2-yloxy)benzoic acidwith borane-THF in tetrahydrofuran at 0 - 20;
Stage #2: with hydrogenchloride in water at 0; for 0.5 h;

Steps:

3 2-(4-Hydroxymethylphenoxy)pyridine

2-(4-Hydroxymethylphenoxy)pyridine Under an atmosphere of argon, 4-(2-pyridyloxy)benzoic acid (1.08g, 5.02mmol) was dissolved in 20mL of dehydrated tetrahydrofuran. Under cooling with ice and stirring, 1mol/L borane-tetrahydrofuran complex (15.1mL, 15.1mmol) was added dropwise for 5 minutes and the mixture was allowed to stand overnight at room temperature. Under cooling with ice, 2mL of 6mol/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 100mL 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. (100%) of the title compound as a pale yellow oil. ¹H-NMR (400MHz, CDCl₃) δ 4.70(2H,s), 6.92(1H,d,J=8.3Hz), 6.99 (1H,ddd,J=7.3,4.9,1.0Hz), 7.13(2H,d,J=8.3Hz), 7.41(2H,d,J=8.8 Hz), 7.67-7.71(1H,m), 8.19(1H,dd,J=4.9,1-5Hz).

References:

EP1348698,2003,A1 Location in patent:Page/Page column 25