Methyl 4-methyloxane-4-carboxylate → (4-Methyloxan-4-yl)methanol

Temperature

-78 °C

At −78° C., 73.3 ml (73.3 mmol, 1.0M in toluene) of diisobutylaluminium hydride were added dropwise to a solution of 5.80 g (36.7 mmol) of methyl 4-methyltetrahydro-2H-pyran-4-carboxylate in 220 ml of toluene such that the internal temperature did not exceed −70° C. The mixture was subsequently stirred at −78° C. for another 90 min and then further at room temperature overnight. The reaction was terminated by addition of 40 ml of methanol and 300 ml of 1N hydrochloric acid. The phases were separated and the aqueous phase was extracted three times with 150 ml of ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product corresponded to the title compound. Yield: 2.14 g (45% of theory)

1. customdid not exceed −70° C
2. customfurther at room temperature
3. customovernight
4. customThe reaction was terminated by addition of 40 ml of methanol and 300 ml of 1N hydrochloric acid
5. customThe phases were separated
6. extractionthe aqueous phase was extracted three times with 150 ml of ethyl acetate
7. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
8. dry with materialdried over magnesium sulphate
9. filtrationfiltered
10. customthe solvent was removed under reduced pressure

ORD record

ord-9d192cfeac254d15b74a839f73e68910

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434690B2