5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 922268

Reaktionsgleichung

Reaktionsgleichung von HRID 922268
Br[Mg][C:3]#[C:4][CH3:5].[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.OS([O-])(=O)=O.[K+]>C1COCC1.[NH4+].[Cl-].CCCCCC>[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:3]#[C:4][CH3:5])=[CH:22][CH:23]=1

Komponenten

7

Edukt 3

HCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 516920Potassium bisulfateHCID 178419101HCID 178419101, Verbindung

Produkt 1

HCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a 250 mL 3-necked RB flask fitted with magnetic stirrer was charged with bromo(prop-1-yn-1-yl)magnesium (42.5 mL, 211 mmol) in THF (30 mL). To the RM was added slowly 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (5.0 g, 100.8 mmol) in THF (20 mL) under nitrogen atmosphere. The RM was stirred at room temperature about 30 minutes. The reaction mixture was diluted with NH4Cl solution and hexane. The aqueous layer was acidified with KHSO4 solution to adjust the pH 2 and extracted with ethyl acetate, washed with water, then dried to obtain the product (5.8 g, yield: 100.0%).

Aufarbeitung

  1. customTo a 250 mL 3-necked RB flask fitted with magnetic stirrer
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b221ad47576d4438b29f562d6346b4b9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278915B2

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