2,3-Dihydro-1-methoxy-1H-inden-2-ol → (1S,2R)-Indene oxide

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Reaction Steps

Trans-1,2-indandiol can be obtained by a reaction of trans-2-bromo-1-indandiol with a dilute aqueous sodium carbonate solution in accordance with the method of A. Gagis, et al [J. Org. Chem., 37, 3181 (1972)]. Cis-1,2-indandiol can be obtained by peroxidation of indene with formic acid in accordance with the method of J. E. Taylor [Synthesis, 1142, (1985)]. Cis-1-methoxy-2-indanol can be obtained by a reaction of cis-1,2-epoxyindan with a copper-pyridine complex in methanol in accordance with the method of M. Imuta, et al [J. Am. Chem. Soc., 101, 3990 (1979)]. As reported by G. H. Posner, et al. [J. Am. Chem. Soc., 99, 8214 (1977)], a mixture of 1-methoxy-2-indanol with a cis/trans ratio of 50/50 can be obtained by a reaction of cis-1,2-epoxyindan with hydrochloric methanol whereas trans-1-methoxy-2-indanol is obtained by a reaction of cis-1,2-epoxyindan with sodium methoxide. The method of G. H. Posner, et al. [J. Am. Chem. Soc., 99, 8208 (1977)] can be used to obtain trans-1-acetoxy-2-indanol by a reaction of cis-1,2-epoxyindan with dilute acetic acid in the presence of neutral alumina.

Provenance & Evidence