Methanol → HCID 57022033, compound

In 600 ml of tetrahydrofuran, containing 3.3 ml methanol were dissolved 47.3 g (82.3 mmol) of (2S,3S)-2-(methoxymethyl)oxy-3-(3-tosyloxypropyl)-1,4-butanediol dibenzoate and the solution was chilled in an ice-bath. To the solution were added, portionwise, 20.65 g (184 mmol) of potassium t-butoxide and the reaction mixture was stirred at room temperature for 2.5 hours. Then, an additional 2.46 g (22 mmol) of potassium t-butoxide and 150 μl of water were added and the reaction was stirred for an additional 30 minutes. Finally, 6 ml of water was added and the mixture was further stirred for 2 hours. The reaction mixture then was poured into a mixture of water and ethyl acetate. The aqueous phase was extracted four times with ethyl acetate and twice with 10% isopropanol-methylene chloride. The organic extracts were combined, dried over magnesium sulfate, carefully concentrated and purified by medium pressure column chromatography using silica gel and 72% ethyl acetate/hexane, 100% ethylacetate. The resulting compound, (2S)-2-[(3S)-tetrahydropyran-3-yl]-2-(methoxymethyl)oxyethanol, was found to be volatile. Thus, evaporation of the solvent was carefully carried out with an aspirator below room temperature. Pure fractions were collected and combined to yield 9.82 g of (2S)-2-[(3S)-tetrahydropyran-3-yl]-2-(methoxymethyl)oxyethanol contaminated with ethyl acetate (34%) as judged by 270 MHz 1H-NMR.

1. temperaturethe solution was chilled in an ice-bath
2. additionTo the solution were added
3. stirringthe mixture was further stirred for 2 hours
4. extractionThe aqueous phase was extracted four times with ethyl acetate
5. dry with materialdried over magnesium sulfate
6. concentrationcarefully concentrated
7. custompurified by medium pressure column chromatography
8. customThus, evaporation of the solvent
9. customwas carefully carried out with an aspirator below room temperature
10. customPure fractions were collected

ORD record

ord-7bca1ebdde8f4f498ecc574c15efb421

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05086062