Sodium Carbonate → 4-Ethoxybut-2-yn-1-ol

HRID 237862

Reaktionsgleichung

Reaktionsgleichung von HRID 237862
[CH2:1]([O:3][CH2:4][C:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:14]CCC[O:10]1)[CH3:2].O.[C:16]1(C)[CH:21]=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:7][O:8][C:9]([CH3:14])=[O:10].[CH3:20][CH2:21][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:1]([O:3][CH2:4][C:5]#[C:6][CH2:7][OH:8])[CH3:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 685294632-(4-Ethoxy-but-2-ynyloxy)-tetrahydro-pyran

Produkt 2

HCID 127868104-Ethoxybut-2-yn-1-olAusbeute 385,9 %HCID 23449302Methyl acetate hexaneAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran (0.5 g, 2.52 mmol) in methanol (10 mL) was added p-toluenesulfonic acid monohydrate (p-TSOH) (0.086 g, 0.454 mmol). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into aqueous sodium carbonate and extracted with methyl acetate. The organic layers were combined, dried (Na2SO4) and concentrated. Silica gel chromatography (1-10% MeOAc/hexane) provided 0.2 g of 4-ethoxy-but-2-yn-1-ol as a clear oil.

Aufarbeitung

  1. extractionextracted with methyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-04be88845d1f4d6d9b54e5d1406b7d8f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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