2-Thenyl alcohol

It was shown further that reducible sulfur compounds could be used as a substrate for the hydrogenation 2-thiophenecarboxaldehyde was reduced to a mixture of 2-thenyl alcohol and 2-methylthiophene. 

J.ll) 2-Thiophenemethanol, thiophene-2-methanol, thenyl alcohol, 2-thenyl alcohol, 2-thiophenecarbinol, 2-hydroxymethylthiophene [636-72-6]... 

Thiophenecarboxaldehyde reacts rapidly with synthesis gas at 185° to give a mixture of thenyl alcohol and 2-methylthiophene. If the reaction is carried out with excess synthesis gas and a large amount of catalyst, 2-methylthiacyclopentane can be secured after a longer reaction period. The completely reduced compound is also readily obtained from either thenyl alcohol or 2-methylthiophene. 

The pinacol rearrangement of sulfonate esters derived from a-hydroxy acetals proceeds by way of intermediate oxonium species, which upon hydrolysis are transformed to the corresponding esters. Sulfonate 24, prepared in optically pure form by classical resolution of the diastereomer-ic mixture obtained from reaction of (-)-camphorsulfonyl chloride with the racemic naph-thenyl alcohol, undergoes thermal [1,2] rearrangement to yield the corresponding ester29. 

Synthesis of Compound I. As shown in Scheme II, 3-(thiophene-3-yl)propyl bromide can be prepared by a two-carbon homologation(2 ) of 3-thenyl bromide via reaction with diethyl malonate to form diethyl 3-thenylmalonate. This is followed by saponification, decarboxylation, reduction of acid to alcohol, (2 ) and replacement of the hydroxyl group with bromide by reacting with PBr3.(22) Compound 2 is synthesized by mono-quaternization of an excess of 4,4 -bipyridine with 3-(thiophene-3-yl)propyl bromide followed by N-methylation with CH3I. All the intermediates in Scheme II have been identified by NMR spectroscopy. 2 has been characterized by NMR and high resolution mass spectroscopy and by electrochemistry. 

The reactions of 2-tlienylchloride and 5-chloro-2-thenylchloride were also investigated (11). It was found that the chloride of 2-thenylchloride is readily replaced by nucleophilic reagents. In analogous reactions, 5-chloro-2-thenyl chloride was converted to the corresponding acetate and thiocyanate. Certain properties of 2-thenylchloride were found to be different from its analog benzylchloride. It is more prone to solvolysis in the presence of bases, consequently alcohols are often undesirable reaction by-products with 2-thenylchloride. 

Relatively straightforward benzene analogue reactivity is found with thenyl halides, alcohols (conveniently preparable by reducing aldehydes) and amines, from, for example, reduction of oximes. One exception is that 2-thenyl Grignard reagents usually react to give 3-substituted derivatives, presumably via a non-aromatic intermediate. ... 

Relatively straightforward benzene-analogue reactivity is found with thenyl halides, alcohols (conveniently preparable by reducing aldehydes) and amines,... 

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