ChemicalBook CAS DataBase List Tetrahydro-4-pyranol

Tetrahydro-4-pyranol synthesis

7synthesis methods

Product Name:Tetrahydro-4-pyranol
CAS Number:2081-44-9
Molecular formula:C5H10O2
Molecular Weight:102.13

29943-42-8

2081-44-9

General procedure for the synthesis of tetrahydropyran-4-ol from tetrahydropyranone: To a tetrahydrofuran (THF, 25 mL) solution of tetrahydropyranone (5.0 g, 50 mmol), which was cooled to 0 °C, a THF (50 mL) suspension of lithium aluminum hydride (LiAlH4, 3.8 g, 0.1 mol) was slowly added. The reaction mixture was stirred at 0 °C for 30 min, followed by sequential addition of water (3.8 mL), 15% aqueous sodium hydroxide (NaOH) solution (3.8 mL) and water (11.4 mL) to quench the reaction. The mixture was filtered and the solid was washed with ethyl acetate (70 mL x 2). The filtrates were combined and evaporated to give tetrahydropyran-4-ol (5.09 g, 99% yield).

29943-42-8 Synthesis

29943-42-8
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2081-44-9
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Yield:2081-44-9 99%

Reaction Conditions:

Stage #1: dihydro-2H-pyran-4(3H)-onewith lithium aluminium hydride in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with sodium hydroxide in tetrahydrofuran;lithium hydroxide monohydrate;

Steps:

8.1

To a solution of 8a (5.Og, 50mmol) in THF (25mL) cooled to O⁰C, was added a suspension Of LiAlH₄ (3.8g, O.lmol) in THF (5OmL) slowly. The resulting mixture was stirred at O⁰C for 30min, then was added water (3.8mL), followed by aqueous 15% NaOH (3.8mL) and water (1 1.4mL). The mixture was filtered and the solid was washed with ethyl ester (70mL^χ2). The combined filtrate was evaporated to afford 8b (5.09g, 99%).

References:

WO2008/88881,2008,A1 Location in patent:Page/Page column 39

67-56-1 Synthesis