Hydrochloric Acid → 3-Methoxypentane-1,5-diol

Temperatur

-5 °C

25 ml of methyl trifluoromethylsulfonate are added to a solution of 30 g of diethyl 3-hydroxyglutarate and 33 ml of 2,6-di-tert-butylpyridine in 500 ml of DCM and the mixture is refluxed for 5 hours. After cooling, 500 ml of a 0.5N solution of HCl are added, the organic phase is decanted and dried over magnesium sulfate and the solvent is evaporated off under vacuum. The solid obtained is taken up with 200 ml of anhydrous THF, the mixture is filtered and the filtrate is then cooled to -5° C. 160 ml of a 1M solution of lithium aluminum hydride in THF are then added slowly and the mixture is stirred for 16 hours, the temperature being allowed to rise to RT. The reaction mixture is cooled to 0° C. and 5.5 ml of water, 18 ml of a 15% solution of NaOH and 5.5 ml of water are added successively. The mineral salts are filtered off and the filtrate is evaporated under vacuum to give the expected product after distillation under reduced pressure. B.p.=104° C. under 1.5 Pa.

1. temperaturethe mixture is refluxed for 5 hours
2. temperatureAfter cooling
3. customthe organic phase is decanted
4. dry with materialdried over magnesium sulfate
5. customthe solvent is evaporated off under vacuum
6. customThe solid obtained
7. filtrationthe mixture is filtered
8. addition160 ml of a 1M solution of lithium aluminum hydride in THF are then added slowly
9. customto rise to RT
10. temperatureThe reaction mixture is cooled to 0° C.
11. addition5.5 ml of water, 18 ml of a 15% solution of NaOH and 5.5 ml of water are added successively
12. filtrationThe mineral salts are filtered off
13. customthe filtrate is evaporated under vacuum

ORD-Eintrag

ord-c06d5392d64949fb9b7e8e9fac97b104

Quelldatensatz

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05696145