Furyl carbinols

Synonyms AI3-01171 BRN 0106291 CCRIS 2922 EINECS 202 626-1 FEMA No. 2491 2-Furan carbinol 2-Furanmethanol Furfural alcohol Furyl alcohol Furyl carbinol 2-Furyl carbi-nol a-Furyl carbinol 2-Furylmethanol 2-Hydroxymethylfuran NCI-C56224 NSC 8843 UN 2874. 

Synonyms 2-Furyl carbinol 2-furanmeth-anol furfural alcohol... 

Furyl Carbinol. See Furfuryl Alcohol in this Section... 

Treatment of a 5-methoxy-2-furyl carbinol (106) with zinc chloride in acetone-water converts it into two products, the 4-ylidenebutenolide (111) and the 4-oxo-2-enoic acid methyl ester (112) in approximately 3 1 ratio (80T3071). The key step in this conversion is the formation of carbonium ion (107) which subsequently adds water to furnish (108). Intermediate (108) is in prototropic equilibrium between (109) and (110). The latter then break down to furnish the final products (Scheme 26). The overall scheme provides a new synthetic route to the 4-ylidenebutenolides, a class of compound that includes many natural substances of biological importance. 

A mixture of i 1. of benzene, 600 g. (6.1 moles) of 2-furyl-carbinol (Org. Syn. 6, 44) (Note 1), 225 g. of fused and powdered sodium acetate, and 650 g. (6.4 moles) of a good grade of acetic anhydride are placed in a 5-I. round-bottom flask (Note 2) fitted with a mechanical stirrer (Org. Syn. 1, 4, Fig. 1 b) and a reflux condenser provided with a calcium chloride Lube. The flask is heated on a steam bath (Note 1) for four hours with stirring to prevent caking of the sodium acetate. 

Furylmethyl acetate has been prepared by heating 2-furyl-carbinol with acetic anhydride alone, or with acetic anhydride and sodium acetate.1... 

A tandem aldol/intramolecular enol cyclization of epoxyaldehydes to form a-furyl carbinols, 127, has been reported <05TL5467>. Only isopropyl methyl ketones or t-butyl methyl ketones have been shown to work in this reaction. The corresponding A-Boc aziridine aldehyde 127 (X = Af-Boc) has also been used to generate an a-amino furan in excellent yield. 

Oxidative rearrangement of furyl carbinols to 6-hydroxy-2/f-pyran-3(6//)-ones, a useful synthon for the preparation of a variety of heterocyclic compounds. A review , Georgiadis, M. R, Albizati, K. F. and Georgiadis, T. M., Org. Prep. Proc. Int., 1992, 24, 95. 

The oxidative ring expansion of furyl carbinols can be accomplished with many of the same oxidants discussed earlier for routine oxidation of the furan ring. As a pyran is formed in the reaction, an obvious application would be for the synthesis of pyranose sugars (Scheme 19). 

Trifluoromethyl)furan 147 was prepared in 67% yield by heating 4-methyl-oxazole 5 and 3,3,3-trifluoropropyne in toluene at 180°C for 13 h (Fig. 3.44). Metalation of 147 at the 2 position with n-butyllithium and subsequent reaction with aldehydes gave 3-(trifluoromethyl)-2-furyl carbinols 148. ... 

Synonyms include Furyl Carbinol, 2-Hydroxy Methyl Furan, 2-Furan Methanol, Furfuryl alcohol resin. Furan resin, FA resin, Poly(furfuryl alcohol). Prepolymers of FA. It is a raw material for organic synthesis, producing levulic acid, resin of various furane kinds in different properties, furfuryl alcohol urea formal resin and phenolic resin. It is a fine solvent for furane resin and oil varnish and pigment as well as used in rocket fuel. It is also used in the production of synthetic fibers, rubber, agricultural chemicals and foundry products. Furfuryl alcohol resins are derivatives of agricultural waste products and complex polymers that are formed in a condensation reaction that occurs when the furfuryl alcohol is acidified. The resins have low viscosity with an odor of furfuryl alcohol. The resin systems are highly reactive and can be catalyzed using a variety of active and latent acidic catalysts. When thermoset, the resins produce polymers that are heat resistant and extremely corrosion resistant to acids, bases and solvents. 

Under treatment with strong acid, 2-furyl(phenyl)carbinol 268 and acetate 269 recyclized into cyclopentenone 270 the related a]kyl(furyl)carbinols gave product of dehydration [84],... 

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