Lithium diisopropylamide → HCID 59609970, Verbindung

An oven-dried 100 mL round-bottom flask was charged with a magnetic stirring bar, tetrahydrofuran (10 mL) and lithium diisopropylamide (2.0M in hexanes, 6.9 mL, 13.8 mmol). The mixture was magnetically stirred and cooled to 0° C. under argon gas. 1-(2-Hydroxybiphenyl-3-yl)ethanone (0.92 g, 4.34 mmol) was added, and the reaction was stirred at 0° C. for 1 hour. A solution of methyl tetrahydro-2H-pyran-4-carboxylate (1.0 g, 6.94 mmol) in tetrahydrofuran (2 mL) was added dropwise over 5 minutes and the reaction was allowed to warm to room temperature overnight. The reaction was quenched by the addition of aqueous 10% hydrochloric acid solution (20 mL) until pH=3. The resulting solution was transferred to a separatory funnel, diluted with water (80 mL), and extracted three times with dichloromethane (100 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give crude 1-(2-hydroxybiphenyl-3-yl)-3-(tetrahydro-2H-pyran-4-yl)propane-1,3-dione as a brown oil. The crude product was used as is without further purification.

1. additionAn oven-dried 100 mL round-bottom flask was charged with a magnetic stirring bar
2. stirringthe reaction was stirred at 0° C. for 1 hour
3. temperatureto warm to room temperature overnight
4. customThe reaction was quenched by the addition of aqueous 10% hydrochloric acid solution (20 mL) until pH=3
5. customThe resulting solution was transferred to a separatory funnel
6. additiondiluted with water (80 mL)
7. extractionextracted three times with dichloromethane (100 mL)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD-Eintrag

ord-d897332b636242b7a55f29df97a2c731

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08557807B2