Diethyl Ether → 2,2,3-Trimethyl-butanol 2,2,3-trimethyl-butanol

Temperatur

0 °C

A 500 mL round-bottom-flask equipped with a stir bar was flushed with Ar and charged with 50 mL dry THF and a 1 M solution of LAH in Et2O (87.5 mL, 87.5 mmol, 0.625 equiv). The solution was cooled to 0° C. with an ice bath and the above ethyl ester (22.1 g, 140 mmol, 1.0 equiv) (approximately a 50% solution in ethylbenzene) was added dropwise at such a rate that the solution did not reflux (required 50 min). After addition of the ester, the reaction was stirred at 0° C. for 2 h and then at ambient temperature for 14 h. The reaction solution was re-cooled to 0° C. and carefully quenched by addition of EtOAc. 1 N NaOH was added until a granular precipitate formed (7.5 mL). The mixture was filtered on a pad of diatomaceous earth which was then washed 3×100 mL Et2O. The organics were combined and dried voer Na2SO4. The solution was decanted and concentrated in vacuo to yield 2,2,3-trimethyl-butanol-2,2,3-trimethyl-butanol as a nearly colorless oil (11.7 g of alcohol in 15.4 g of a mix with ethylbenzene). The crude product was used without further purification.

1. customA 500 mL round-bottom-flask equipped with a stir bar
2. customwas flushed with Ar
3. additioncharged with 50 mL dry THF
4. temperaturedid not reflux (required 50 min)
5. waitat ambient temperature for 14 h
6. temperatureThe reaction solution was re-cooled to 0° C.
7. customcarefully quenched by addition of EtOAc
8. addition1 N NaOH was added until a granular precipitate
9. customformed (7.5 mL)
10. filtrationThe mixture was filtered on a pad of diatomaceous earth which
11. washwas then washed 3×100 mL Et2O
12. dry with materialdried voer Na2SO4
13. customThe solution was decanted
14. concentrationconcentrated in vacuo

ORD-Eintrag

ord-8eebb889aef844b18516b3f6d7473660

Quelldatensatz

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06787540B2