2,3-Dihydro-1-methoxy-1H-inden-2-ol → (1S,2R)-Indene oxide
Reaction equation
[CH3:1][O:2][CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[OH:12]>CO>[O:12]1[C@@H:4]2[CH2:5][C:6]3[C:11]([C@H:3]12)=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH3:1][O:2][C@@H:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@H:4]1[OH:12]Participants
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
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.
Sources & evidence
- ORD record
- ord-cff3b08da0314bc8861f6fc6a453a2a5
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05648534
Reaction notes
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