Potassium Iodide → 4-Methyl-4-phenyl-tetrahydro-pyran

3-Methyl-3-phenyl-pentane-1,5-diol (3.88 g, 20 mmol), Ag2O (6.95 g (30 mmol), potassium iodide (0.66 g, 4 mmol) were suspended in 50 mL DCM and treated with a solution of p-toluenesulfonyl chloride (4.19 g, 22 mmol) in 30 mL DCM. The mixture was allowed to stir under nitrogen atmosphere for 16 h. The crude reaction mixture was applied on a short plug of silica gel column and the product was collected by washing with DCM. The solvent was evaporated and the residue was dissolved in dry THF (30 mL) and added drop wise to a suspension of NaH (0.8 g of 60% suspension in mineral oil, 20 mmol) in THF (30 ml). The reaction mixture was allowed to stir at room temperature for 24 h and was then diluted with 60 mL ether and washed with water (60 mL). The aqueous phase was washed once with ether (30 mL) and the organic extracts were combined, washed with brine, dried over Na2SO4 and the solvent was evaporated by rotary evaporation. The product was purified by flash chromatography on silica gel column using 0-5% hexane/ethylacetate solvent mixture as the mobile phase. MS: m/z 177.1 (M++1).

1. customThe crude reaction mixture
2. customthe product was collected
3. washby washing with DCM
4. customThe solvent was evaporated
5. dissolutionthe residue was dissolved in dry THF (30 mL)
6. additionadded drop
7. stirringto stir at room temperature for 24 h
8. washwashed with water (60 mL)
9. washThe aqueous phase was washed once with ether (30 mL)
10. washwashed with brine
11. dry with materialdried over Na2SO4
12. customthe solvent was evaporated by rotary evaporation
13. customThe product was purified by flash chromatography on silica gel column

ORD record

ord-21c69057cbb148e49da8f36283d49210

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420055B2