(5-PHENYL-FURAN-2-YL)-METHANOL synthesis

12synthesis methods

Product Name:(5-PHENYL-FURAN-2-YL)-METHANOL
CAS Number:22078-90-6
Molecular formula:C11H10O2
Molecular Weight:174.2

57489-93-7 Synthesis

57489-93-7
17 suppliers
$81.37/1g

22078-90-6
25 suppliers
$45.00/10mg

Yield:22078-90-6 80%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;N,N-dimethyl-formamide at -10 - 0; for 2 h;Inert atmosphere;

Steps:

2.2.1. General procedure for the synthesis of title compounds 3a-3k

General procedure: According to the reported literature [10aec], Intermediates 5-substituted phenyl-2-furoic acid 7a-7k were prepared fromsubstituted aniline by Meerwein arylation reaction, and the corresponding5-phenylfuran-2-carbonyl chloride were prepare usingSOCl2 as solvent and reactant. A solution of 5-phenylfuran-2-carbonyl chloride (5.0 mmol, 1 equiv) was prepared in dry THFand cooled to 10 C under nitrogen atmosphere. Sodium borohydride(6.0 mmol, 1.2 equiv) was added to the THF solution andthe reaction mixture was stirred for 2 h at 0 C. The reaction wasquenched by adding 10% aqueous ammonium chloride solution.THF was distilled off and the residue was diluted by adding chloroformand water. The product was extracted with three portions ofchloroform and the organic layers were combined, dried overanhydrous MgSO4, filtered and concentrated to get the crudealcohol. It was purified by column chromatography (silica gel,hexane and chloroform as eluents) to isolate a colorless liquid (80%yield).

References:

Lin, Yinuo;Ahmed, Wasim;He, Min;Xiang, Xuwen;Tang, Riyuan;Cui, Zi-Ning [European Journal of Medicinal Chemistry,2020,vol. 207]

13803-39-9 Synthesis