Reaktion #64166

Reaktionsgleichung

1,1,1-trifluoroacetone

4-(4-pyridylsulfonyl)phenylacetylene

diisopropylamine

n-butyllithium

→

title compound

Ausbeute 50.0%

4,4,4-Trifluoro-3-hydroxy-3-methyl-1-[4-(pyrid-4-ylsulfonyl)phenyl]but-1-yne

Ausbeute 50.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturbefore being cooled to -78° C
2. 2
   workup.STIRRINGThe mixture was stirred for an additional 15 minutes at -78° C
3. 3
   workup.STIRRINGAfter stirring the mixture at -78° C. for 20 minutes
4. 4
   Sonstigeit was quenched with water
5. 5
   Temperaturwarmed to ambient temperature
6. 6
   SonstigeThe solution was evaporated
7. 7
   Sonstigethe resulting residue was partitioned between water and ethyl acetate
8. 8
   SonstigeThe ethyl acetate layer was separated
9. 9
   Waschenwashed (brine)
10. 10
    Sonstigedried
11. 11
    Sonstigeevaporated
12. 12
    SonstigeThe resulting brown oil was purified by chromatography, with ethyl acetate

Vorschrift

To a solution of diisopropylamine (0.37 mL, 2.66 mmol) in tetrahydrofuran (11 mL) at -20° C. was added n-butyllithium (0.9 mL of 2.5M solution in hexanes, 2.25 mmol) and the resulting solution was stirred for 25 minutes at -20° C. before being cooled to -78° C. To this was added a solution of 4-(4-pyridylsulfonyl)phenylacetylene (0.5 g, 2.05 mmol) in tetrahydrofuran (3 mL) over a five minute period. The mixture was stirred for an additional 15 minutes at -78° C. To this was added 1,1,1-trifluoroacetone (0.20 mL, 2.25 mmol) in one portion. After stirring the mixture at -78° C. for 20 minutes, it was quenched with water, warmed to ambient temperature and the pH adjusted to 7.0 with saturated aqueous NH4Cl . The solution was evaporated and the resulting residue was partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed (brine), dried and evaporated. The resulting brown oil was purified by chromatography, with ethyl acetate:dichloromethane as the eluent (1:5), to give the title compound as a white solid (0.36 g, 50%); mp 122°-125° C.; NMR (CDCl3): 1.73 (s,3, CH3), 3.37 (s,1, OH), 7.61 (d,2, J=8.2, At), 7.76 (d,2, J=5.1, Ar), 7.93 (d,2, J=4); MS: m/z=356(M+ 1). Analysis for C16H12F3NO3S: Calculated: C, 54.08; H, 3.40; N, 3.94; Found: C, 53.99; H, 3.41; N, 3.75.

Quelle