3,4-dihydro-2H-pyran → 2H-Pyran, tetrahydro-2-[(1-methyl-3-butynyl)oxy]-

HRID 872884

Reaktionsgleichung

Reaktionsgleichung von HRID 872884
[CH3:1][CH:2]([OH:6])[CH2:3][C:4]#[CH:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][CH:2]([O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)[CH2:3][C:4]#[CH:5]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 929154-Pentyn-2-olHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Produkt 1

HCID 108990812H-Pyran, tetrahydro-2-[(1-methyl-3-butynyl)oxy]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(+/−)-4-Pentyn-2-ol (5.58 ml, 59.4 mmol) and 3,4-dihydro-2H-pyran (8.08 ml, 89 mmol) were dissolved in DCM (100 ml). 4-Toluenesulfonic acid pyridine salt (1.494 g, 5.94 mmol) was added and the resulting mixture was stirred for 4 h at RT with CaCl2-tube. The mixture was concentrated. 50 ml of diethyl ether was added, extracted with brine and dried with MgSO, filtered and evaporated. The product was used in the subsequent steps without further purifications. LC-MS: [M+1]=169.23.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. addition50 ml of diethyl ether was added
  3. extractionextracted with brine
  4. dry with materialdried with MgSO
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4d067790cf264ad5b83d868f70cd05ac
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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