Dimethyl Sulfoxide → HCID 10535409, Verbindung

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Reaktionsgleichung

C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[N:13]=[C:14]([CH2:21][OH:22])[CH:15]=[C:16]2[CH:20]=[CH:19][O:18][C:17]=12.C(=O)=O.CC(C)=O>C(Cl)Cl>[Cl:11][C:12]1[N:13]=[C:14]([CH:21]=[O:22])[CH:15]=[C:16]2[CH:20]=[CH:19][O:18][C:17]=12

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Oxalyl chloride (3.1 mL, 35 mmol) is dissolved in 200 mL CH2Cl2 in a dried flask under N2. The flask is placed in a dry-ice/acetone bath at −78° C., DMSO (4.95 mL, 70 mmol) in 10 mL CH2Cl2 is added drop-wise, and the mixture is stirred for 20 min. (7-Chlorofuro[2,3-c]pyridin-5-yl)methanol (C4) (5.5 g, 30 mmol) in 10 mL CH2Cl2 is added, and the reaction is stirred 30 min at −78° C. TEA (21.3 mL, 153 mmol) is then added. The reaction is stirred 30 min in the dry-ice/acetone bath, an ice bath replaces the dry-ice/acetone bath, and the reaction is stirred 1 h and is washed with 100 mL 1:1 saturated NaCl/NaHCO3. The organic layer is dried over anhydrous K2CO3, filtered, and concentrated in vacuo to afford 7-chlorofuro[2,3-c]pyridine-5-carbaldehyde (C6) as a pale yellow solid (97% yield). MS (EI) for C8H4ClNO2 m/z: 181 (M)+.

Aufarbeitung

customThe flask is placed in a dry-ice/acetone bath at −78° C.
additionis added
stirringthe reaction is stirred 1 h
washis washed with 100 mL 1:1 saturated NaCl/NaHCO3
dry with materialThe organic layer is dried over anhydrous K2CO3
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-6f3542f8702f4cb1a63ebdbf74cb50df
Quelldatensatz: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06911543B2

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