Reaktion #58519

Reaktionsgleichung

product

5-Methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[α]pentalene-2-carboxylic acid ethyl ester

hydroquinone

NCS

→

6-Chloro-5-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[α]pentalene-2-carboxylic acid ethyl ester

Lösungsmittel

water

CHCl3

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude reaction mixture
2. 2
   Extraktionextracted with EtOAc (3×3 ml)
3. 3
   TrocknenThe organic layer was dried (MgSO4)
4. 4
   Sonstigepurified by preparative TLC

Vorschrift

The product of step c) (74.2 mg, 0.30 mmol) was placed in a vial and diluted with CHCl3 (740 μl) and AcOH (740 μl). Next, hydroquinone (−5 mg) was added followed by NCS (41.3 mg, 0.31 mmol) and the contents were heated to 40° C. for 6 hours. The crude reaction mixture was diluted with water (2 ml) and extracted with EtOAc (3×3 ml). The organic layer was dried (MgSO4) and purified by preparative TLC using hexanes/EtOAc 50:50 providing subtitled product. MS calculated for C13H16ClNO2S+H 286, observed 286.

Quelle