Propargyl bromide → HCID 21553175, Verbindung

HRID 268048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268048
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:15](Br)[C:16]#[CH:17]>CN(C)C=O.O>[CH2:17]([O:12][CH2:11][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1)[C:16]#[CH:15]

Komponenten

6

Edukt 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 27761742,3-Dihydro-1,4-benzodioxin-6-methanol

Produkt 1

HCID 21553175HCID 21553175, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 16.6 g of 1,4-benzodioxan-6-methanol in 20 ml of dimethylformamide is added dropwise with stirring to a suspension of 12.5 g of sodium hydride in 75 ml of dimethylformamide. 11.8 g of propargyl bromide are then added dropwise. The mixture is stirred for 3 hours at room temperature, cooled in an ice-bath, decomposed with 20 ml of ice-water, diluted with 150 ml of water and extracted three times with 150 ml of diethyl ether each time. The ether extract is washed with water, dried over sodium sulphate and evaporated. The oily residue is chromatographed on silica gel using benzene as the elution agent. There is obtained 6-[(2-propynyloxy)methyl]-1,4-benzodioxan; nD24 = 1.5487.

Aufarbeitung

  1. temperaturecooled in an ice-bath
  2. extractionextracted three times with 150 ml of diethyl ether each time
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe oily residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-669c6c933113477ba0e8bbe431746f5e
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03946040

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