ChemicalBook CAS DataBase List 2,2-DIMETHYLTETRAHYDROPYRAN-4-ONE

2,2-DIMETHYLTETRAHYDROPYRAN-4-ONE synthesis

12synthesis methods

Product Name:2,2-DIMETHYLTETRAHYDROPYRAN-4-ONE
CAS Number:1194-16-7
Molecular formula:C7H12O2
Molecular Weight:128.17

4H-Pyran-4-one, 2,3-dihydro-2,2-dimethyl-

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2H-Pyran-4-ol, 4-[3-fluoro-5-(2-naphthalenyloxy)phenyl]tetrahydro-2,2-dimethyl-

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1194-16-7
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Yield: 74%

Reaction Conditions:

palladium in ethanol

Steps:

11 EXAMPLE 11
The 4-[5-fluoro-3-(naphth-2-yloxy)phenyl]-4-hydroxy-2,2-dimethyltetrahydropyran used as a starting material was obtained as follows: A mixture of 2,3-dihydro-2,2-dimethylpyran-4-one (2.72 g, J. Org. Chem., 1963, 687), 10% palladium-on-charcoal catalyst (0.27 g) and ethanol (80 ml) was stirred under an atmosphere of hydrogen for 6 hours. The mixture was filtered and the filtrate was evaporated. There was thus obtained 2,2-dimethyltetrahydropyran-4-one (2.05 g, 74%), as a liquid. IR Spectrum 1730 cm^-1 (C=O). Using a similar procedure to that described in the last paragraph of the portion of Note b. below Table III in Example 8 which is concerned with the preparation of starting materials, the organo-lithium derivative from 3-bromo-5-fluorophenyl 2-naphthyl ether was reacted with 2,2-dimethyltetrahydropyran-4-one to give the required starting material in 68% yield as an oil, NMR Spectrum (CDCl₃, δ values) 1.25 (s, 3H), 1.50 (s, 3H), 1.75 (s, 1H), 1.8-2.5 (m, 4H), 3.75-4.25 (m, 2H), 6.5-8.0 (m, 10H).

References:

Imperial Chemical Industries;ICI Pharma US5208259, 1993, A

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1194-16-7
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$16.00/250mg

References