ChemicalBook CAS DataBase List (4-THIEN-3-YLPHENYL)METHANOL

(4-THIEN-3-YLPHENYL)METHANOL synthesis

9synthesis methods

Product Name:(4-THIEN-3-YLPHENYL)METHANOL
CAS Number:160278-20-6
Molecular formula:C11H10OS
Molecular Weight:190.26

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Yield:160278-20-6 65%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 4 h;Inert atmosphere;

Steps:

45.1 Preparation of [4-(3-thienyl)-phenyl]-methanol

Under nitrogen atmosphere, at 0 °C, to a stirring mixture of L1AIH4 (2.0 M THF solution, 3.92 mL, 7.84 mmol) in dry THF (6.0 mL), commercially available 4-(3-thienyl)- benzoic acid (0.4 g, 1.96 mmol) in dry THF (30 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0 °C H₂0 (0.30 mL), 3.0 M KOH solution (0.30 mL) and H₂0 (1.0 mL) were very slowly added. The mixture was stirred for 1 h at 0 °C, filtered to remove the solid residue, and the organic phase dried over Na₂S0₄. The organic solution was again filtered and concentrated to dryness, affording the title compound (0.222 g, 65%), which was used in the next step without any further purification. ¹H NMR (DMSO-d₆): δ 4.51 (d, J = 5.75 Hz, 2H), 5.17 (t, J = 5.75 Hz, 1H), 7.35 (d, J = 8.1 Hz, 2H), 7.52 - 7.57 (m, 1H), 7.63 (dd, J = 2.9, 5.0 Hz, 1H), 7.67 (d, J = 8.1 Hz, 2H), 7.81 - 7.86 (m, 1H).

References:

WO2013/78430,2013,A1 Location in patent:Paragraph 0357