Reaktion #78287

Reaktionsgleichung

EtOAc

Trimethylsilyliodide

CH3CN

alcohol

1-(1-Hydroxy-1-thiophen-2-yl-methyl)cyclobutanecarboxylic acid ethyl ester

CH3CN

NaOH

→

ester

1-Thiophen-2-yl-methylcyclobutanecarboxylic acid ethyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas kept between 4-10° C.
2. 2
   workup.STIRRINGAfter stirring for 2 h at 23° C. the reaction
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

Trimethylsilyliodide (20 g, 100 mmol) was added to CH3CN (10 mL) at 0° C. and the mixture was allowed to stir 5 min. A solution of alcohol 2 (5 g, 20 mmol) in CH3CN (10 mL) was added slowly while the temperature was kept between 4-10° C. and the reaction was allowed to warm to 23° C. After stirring for 2 h at 23° C. the reaction was judged complete via TLC analysis. The mixture was poured into 3N NaOH at 0° C. and EtOAc was added. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. FCC (silica gel, 1:1 hexane/CH2Cl2) gave 2.3 g of the above named ester 3.

Quelle