Thionyl Chloride → 4,5,6,7-Tetrahydro-1-benzothiophen-7-one

HRID 402128

Reaktionsgleichung

Reaktionsgleichung von HRID 402128
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:2]1.S(Cl)(Cl)=O>COCCOCCOC.N1C=CC=CC=1>[S:1]1[C:2]2[C:9](=[O:11])[CH2:8][CH2:7][CH2:6][C:3]=2[CH:4]=[CH:5]1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 110411434-(Thiophen-3-yl)butanoic acid

Produkt 1

HCID 103746284,5,6,7-Tetrahydro-1-benzothiophen-7-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The product from Step D (1.8 g, 11.0 mmol) was dissolved in 2-methoxyethyl ether (2 mL) and added thionyl chloride (0.89 mL, 12.2 mmol) and pyridine (1 drop) and heated to 70° C. for 24 hours. The mixture was purified by column chromatography (silica gel, 0-15% ethyl acetate/hexanes as an eluent) to provide 5,6-dihydro-4H-benzothiophen-7-one (1.16 g, 72%): 1H NMR (500 MHz, CDCl3) δ 7.61 (d, J=4.9 Hz, 1H), 6.97 (d, J=4.9 Hz, 1H), 2.89-2.87 (m, 2H), 2.63-2.60 (m, 2H), 2.21-2.16 (m, 2H).

Aufarbeitung

  1. customThe mixture was purified by column chromatography (silica gel, 0-15% ethyl acetate/hexanes as an eluent)

Quellen und Nachweise

ORD-Eintrag
ord-54b938917b6945f0818ce0d375c7c28c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741901B2

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