Reaktion #1111297

Reaktionsgleichung

Acetic acid

NaCN

42a

5-[3-((S)-2-{4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl)-propyl]-thiophene-2-carbaldehyde

→

title compound

Ausbeute 99.0%

5-[3-((S)-2-{4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl)-propyl]-thiophene-2-carboxylic acid methyl ester

Ausbeute 99.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered through Celite
2. 2
   Waschenwashing with ethyl acetate
3. 3
   WaschenThe filtrate was washed with water (20 mL)
4. 4
   Extraktionthe aqueous layer was further extracted with ethyl acetate (20 mL)
5. 5
   TrocknenThe combined ethyl acetate solution was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

Acetic acid (12 μL, 0.21 mmol), NaCN (25 mg, 0.51 mmol) and MnO2 (152 mg, 1.7 mmol) were added to a mixture of 42a (43 mg, 0.084 mmol) in methanol (0.5 mL). The mixture was stirred for 18 h and then was filtered through Celite, washing with ethyl acetate. The filtrate was washed with water (20 mL) and the aqueous layer was further extracted with ethyl acetate (20 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated to give the title compound (45 mg, 0.083 mmol, 99%).

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