(5-nitro-1-benzofuran-2-yl)methanol synthesis

5synthesis methods

Product Name:(5-nitro-1-benzofuran-2-yl)methanol
CAS Number:90322-48-8
Molecular formula:C9H7NO4
Molecular Weight:193.16

10242-12-3
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$12.00/100mg

90322-48-8
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$244.00/500mg

Yield:90322-48-8 98%

Reaction Conditions:

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

Steps:

2.9. Typical procedure for the preparation of benzofuran-2-ylmethanols: synthesis of the benzofuran-2-ylmethanol

General procedure: In a flame dried two-necked round bottom flask charged with a stir bar, LiAlH₄ in THF (2 M, 3.4 mL, 6.79 mmol, 1.1 equiv.) was added dropwise to a solution of benzofuran-2-carboxylic acid (1.0 g, 6.17 mmol, 1.0 equiv.) in anhydrous THF (20 mL) at 0°C under argon. The mixture was allowed to warm to room temperature and stirred for 2 hours. After the complete consumption of the starting material (TLC, hexane/EtOAc 90/10 v/v), the reaction was cooled down to 0°C and quenched by slow addition of an 80 percent aqueous MeOH solution. The mixture was extracted with AcOEt, washed with brine and the combined organic phase was dried over MgSO₄, filtered, and concentrated in vacuo. The residue was purified by chromatography on SiO₂ (25-40 μm), eluting with a 85/15 (v/v) n-hexane/AcOEt mixture (Rf = 0.24) to afford 0.713 g of benzofuran-2-ylmethanol as a pale yellow oil (0.713 g, 80% yield).

References:

Arcadi, Antonio;Calcaterra, Andrea;Chiarini, Marco;Fabrizi, Giancarlo;Fochetti, Andrea;Goggiamani, Antonella;Iazzetti, Antonia;Marrone, Federico;Marsicano, Vincenzo;Serraiocco, Andrea [Synthesis,2021,vol. 54,# 3,p. 741 - 753] Location in patent:supporting information

69604-00-8 Synthesis