Ethyl Acetate → HCID 57638733, Verbindung

Temperatur

-5 °C

A clean oven dried flask was charged with the 6-(4-nitro-phenyl)-hexane-2,4-dione (3.7 g, 15.72 mmol), dry CH2Cl2 (20 ml) followed by bisTMS ethylene glycol (38.5 ml, 157.3 ml) were added to the flask and the resulting solution was cooled to −5° C. with stirring under argon. TMSOTf (300 μl) was added to the reaction mixture and the solution was stirred at −5° C. for 6 h. Reaction was quenched with pyridine (10 ml) and poured into sat. NaHCO3. The mixture was extracted with EtOAc and the organic layer was washed with water, brine, dried (Na2SO4) and concentrated to give a yellow solid. The solid was triturated with hexanes to give a free flowing pale yellow solid (3.5 g, 72%) which was dissolved in EtOAc (50 ml) and hydrogenated on a Parr shaker starting with 50 psi of hydrogen pressure. After two hours the reaction was filtered through a pad of celite, the celite was washed thoroughly with CH2Cl2MeOH and combined organics were concentrated to give title compound (1.46 g, 100%) as an oil that solidifies upon standing.

1. customA clean oven dried flask
2. additionwere added to the flask
3. stirringthe solution was stirred at −5° C. for 6 h
4. customReaction
5. customwas quenched with pyridine (10 ml)
6. additionpoured into sat. NaHCO3
7. extractionThe mixture was extracted with EtOAc
8. washthe organic layer was washed with water, brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated
11. customto give a yellow solid
12. customThe solid was triturated with hexanes
13. customto give
14. filtrationAfter two hours the reaction was filtered through a pad of celite
15. washthe celite was washed thoroughly with CH2Cl2MeOH
16. concentrationcombined organics were concentrated

ORD-Eintrag

ord-10e054fedaa442fba2a66bca84ba37d8

Quelldatensatz

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07521425B2