Tetrahydrofuran → 2-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol

HRID 384540

Reaktionsgleichung

Reaktionsgleichung von HRID 384540
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:18]1([CH2:19][CH:20]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[OH:21])[CH:22]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 3

HCID 8028Tetrahydrofuran3×HCID 215472-Phenyl-1,3-dithianeHCID 178418339Butyllithium

Produkt 1

HCID 222719962-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanolAusbeute 71 %

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a solution of 2-phenyl-[1,3]-dithiane (65) (4.0 g, 20.4 mmol) in THF at −30° C. was added a 1.6 M solution of n-butyllithium in THF (15.3 mL, 24.4 mmol). After stirring for 30 minutes at −30° C., a solution of phenylacetylaldehyde (2.45 g, 20.4 mmol) in tetrahydrofuran was added dropwise at −30° C. The resulting reaction mixture was stirred for another hour at 0° C. The reaction was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The combined organic extracts were washed with saturated NH4Cl solution, brine and dried over Na2SO4. After filtrating and concentrating, the crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes), to afford 2.63 g (71%) of the title compound (66). 1H NMR (CDCl3, 400 MHz): δ1.97 (m, 2H), 2.23 (dd, J=4.0, 1.2 Hz, 1H), 2.43 (dd, J=13.6, 10.2 Hz, 1H), 2.77 (m, 4H), 3.02 (d, J=13.6 Hz, 1H), 4.07 (m, 1H), 7.44-7.13 (m, 8H), 8.02 (dd, J=8.4, 1.4 Hz, 2H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred for another hour at 0° C
  3. customThe reaction was quenched with saturated NH4Cl solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with saturated NH4Cl solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtrating
  8. concentrationconcentrating
  9. customthe crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes),

Quellen und Nachweise

ORD-Eintrag
ord-cc2c40d9238e41cc84ed50ffaa49eb67
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367722B2

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