Tetrahydrofuran → (R)-3,3-dimethylbutane-1,2,4-triol

온도

0 °C

(R)-3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one (3.21 g, 24.7 mmol) was added to 30 mL THF and cooled to 0° C. Lithium aluminum hydride (24.7 mL, 24.7 mmol) was added slowly and the reaction was warmed to ambient temperature and heated for 6 hours at reflux, during which a heterogeneous mixture of white solids formed. The reaction was cooled to ambient temperature, and 1 mL water was added, followed by the addition of 1 mL of a 15% NaOH aqueous solution (w/v) and 3 mL of water, and the reaction was stirred overnight. The reaction was passed through Celite and filtered, rinsed with copious amounts of ethyl acetate, then dried over Na2SO4. The mixture was filtered, the filtrate was concentrated, and excess water was azeotroped with toluene-DCM (1-1). The residue was dried under high vacuum for 1 hour to yield 2.4 g of the desired product as a clear thick oil.

1. temperaturethe reaction was warmed to ambient temperature
2. temperatureheated for 6 hours
3. temperatureat reflux, during which
4. additiona heterogeneous mixture of white solids
5. customformed
6. temperatureThe reaction was cooled to ambient temperature
7. filtrationfiltered
8. washrinsed with copious amounts of ethyl acetate
9. dry with materialdried over Na2SO4
10. filtrationThe mixture was filtered
11. concentrationthe filtrate was concentrated
12. customexcess water was azeotroped with toluene-DCM (1-1)
13. customThe residue was dried under high vacuum for 1 hour

ORD 기록

ord-527cc687455b480ba4e510b56ae2205e

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08987251B2