Cyclohexanone → HCID 59836431, Verbindung

Temperatur

-78 °C

Cyclohexanone Compound 2a (1.37 g, 14.0 mMol) in THF (5 mL) was added dropwise to a solution of LHMDS (16.0 mL, 16.0 mMol) in anhydrous THF (25 mL) at −78° C. under a N2 atmosphere. The solution was stirred at −78° C. for about 1 hr. Methyl dimethoxyacetate Compound 11a (1.88 g, 14.0 mMol) in anhydrous THF (5 mL) was then added dropwise. The reaction mixture was stirred while warming to r.t. over a period of about 15 hrs, then the reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford 2-(2,2-dimethoxy-acetyl)-cyclohexanone Compound 11b (1.82 g, 65%).

1. stirringThe reaction mixture was stirred
2. temperaturewhile warming to r.t. over a period of about 15 hrs
3. customthe reaction was quenched with water (5 mL)
4. additionThe organic layer was diluted with EtOAc (100 mL)
5. washwashed with water and brine
6. customThe organic layer was separated
7. dry with materialdried with anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto yield a crude product as an oil
11. customThe oil was purified by flash chromatography (eluted with 10% EtOAc in hexane)

ORD-Eintrag

ord-82e679f6918c48e7a2ce22440d538ded

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07452997B2