4-methoxy-alpha-pyridylbenzyl alcohol synthesis

14synthesis methods

Product Name:4-methoxy-alpha-pyridylbenzyl alcohol
CAS Number:27805-39-6
Molecular formula:C13H13NO2
Molecular Weight:215.25

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Yield: 82%

Reaction Conditions:

in tetrahydrofuran at -78 - 20; for 0.25 h;

Steps:

(4-Methoxyphenyl)(pyridin-2-yl)methanol (8i)
To a solution of picolinaldehyde (1.08 g, 10.1 mmol) in THF (50 mL) was added dropwise 4-methoxyphenylmagnesium chloride (20 mL, 10 mmol, 0.5 M in THF) at -78 °C. The reaction mixture was stirred at -78 °C for 5 min, and then room temperature for 10 min. The reaction was quenched by the addition of saturated aqueous ammonium chloride, and then extracted with ethyl acetate. The conbined organic layer was washed with brine, and dried over Na₂SO₄. The mixture was concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (Hexane:AcOEt = 1:1) to give 8i as a colorless solid (1.77 g, 82%). ¹H NMR spectroscopic data are identical to those reported in the literature.² Mp 130-132 °C. ¹H NMR (400 MHz, CDCl₃) δ 3.78 (3H, s), 5.21 (1H, d, J = 3.7 Hz), 5.71 (1H, d, J = 3.7 Hz), 6.87 (2H, d, J = 8.5 Hz), 7.13 (1H, d, J = 7.3 Hz), 7.18 (1H, dd, J = 7.3, 5.5 Hz), 7.28 (2H, d, J = 8.5 Hz), 7.61 (1H, ddd, J = 7.3, 7.3, 1.8 Hz), 8.56 (1H, d, J = 5.5 Hz). ¹³C NMR (100 MHz, CDCl₃) δ 55.2, 74.5, 113.9, 121.3, 122.3, 128.4, 135.5, 136.8, 147.7, 159.2, 161.2. IR (ATR) n_max 3173, 1607, 1591, 1569, 1515, 1466, 1436, 1333, 1304, 1255, 1178, 1115, 1052, 1031, 1000 cm^-1. MS (ESI) 216 (M+H)⁺. HRMS (ESI) calcd for C₁₃H₁₄NO₂ (M+H)⁺ 216.10245, found 216.10212.

References:

Nishigaya, Yosuke;Umei, Kentaro;Watanabe, Daisuke;Kohno, Yasushi;Seto, Shigeki [Tetrahedron,2016,vol. 72,# 12,p. 1566 - 1572] Location in patent:supporting information

109-04-6 Synthesis