Reaktionsgleichung
[C:1]([Mg]Br)#[C:2][CH3:3].[OH:6][C:7]1[CH:23]=[CH:22][C:10]([CH:11]=[C:12]2[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]2=[O:21])=[CH:9][CH:8]=1>C1COCC1>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:11]([CH:12]2[C:13](=[O:21])[O:14][C:15]([CH3:20])([CH3:19])[O:16][C:17]2=[O:18])[C:1]#[C:2][CH3:3])=[CH:22][CH:23]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of 1-propynyl magnesium bromide in THF (0.5 N, 322 mL, 161.28 mmol) is added a solution of 5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (20 g, 80.64 mmol) in THF (200 mL) by cannula under a nitrogen atmosphere. Over the course of the addition, the reaction mixture changed to a thick, yellow suspension. After addition is compete, the reaction mixture is stirred for 15 minutes at 50° C., quenched with aqueous NH4Cl, and acidified to pH ˜2 with 2 N HCl. The mixture is extracted with EtOAc (2×300 mL) and the combined extracts are washed with saturated brine, dried over MgSO4, filtered, and concentrated to a yellow solid (20 g, 86%). The product is carried on crude.
Aufarbeitung
- additionOver the course of the addition
- additionAfter addition
- customquenched with aqueous NH4Cl
- extractionThe mixture is extracted with EtOAc (2×300 mL)
- washthe combined extracts are washed with saturated brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to a yellow solid (20 g, 86%)
Quellen und Nachweise
- ORD-Eintrag
- ord-1c42dd34b9884fbbbf79e3449e978d24
- Quelldatensatz
- uspto-grants-2013_02
- Patentnummer
- US08383642B2
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