p-Toluenesulfonic acid → 5-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

HRID 346255

Reaktionsgleichung

Reaktionsgleichung von HRID 346255
[CH3:1][C:2]([CH3:9])([CH3:8])[CH:3]([CH2:6][SH:7])[CH2:4][OH:5].[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[CH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:2]([CH:3]1[CH2:4][O:5][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([C:10]#[CH:11])=[CH:13][CH:14]=2)[S:7][CH2:6]1)([CH3:9])([CH3:8])[CH3:1]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 27716454-EthynylbenzaldehydeHCID 19990620HCID 19990620, Verbindung

Produkt 1

HCID 199906265-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 3,3-dimethyl-2-mercaptomethylbutan-1-ol (1.46 g), 4-ethynylbenzaldehyde (1.30 g) (W.B. Austin et al. J. Org. Chem., 1981, 46. 2280) and para-toluenesulphonic acid (10 mg) in benzene (50 ml) was heated to reflux overnight under Dean and Stark conditions. The resulting solution was evaporated under reduced pressure and the residue was purified on silica. Elution with 4:1 hexane: dichloromethane gave 5-t-butyl-2-(4-ethynylphenyl)-1,3-oxathiane as a mixture of isomers.

Aufarbeitung

  1. temperatureto reflux overnight under Dean and Stark conditions
  2. customThe resulting solution was evaporated under reduced pressure
  3. customthe residue was purified on silica
  4. washElution with 4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-c9cf745b0adf40639ca7aee192e3a0dc
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061726

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