Diethyl Ether → 4,4,4-Trifluoro-3-hydroxy-3-fluoromethyl-1-(4-phenylsulfonylphenyl)but-1-yne

HRID 35893

Reaktionsgleichung

Reaktionsgleichung von HRID 35893
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[CH:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[F:23][C:24]([F:30])([F:29])[C:25]([CH2:27][F:28])=[O:26].C(OCC)C>O1CCCC1>[F:23][C:24]([F:30])([F:29])[C:25]([OH:26])([CH2:27][F:28])[C:17]#[C:16][C:13]1[CH:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 27605651,1,1,3-TetrafluoroacetoneHCID 199393204-PhenylsulfonylphenylethyneHCID 178418339Butyllithium

Produkt 1

HCID 199393234,4,4-Trifluoro-3-hydroxy-3-fluoromethyl-1-(4-phenylsulfonylphenyl)but-1-yne

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (-78° C.) solution of 4-phenylsulfonylphenylethyne (1.68 g) in anhydrous tetrahydrofuran (70 mL) was added n-butyl lithium (3.06 mL of a 2.5 M solution in hexanes). The solution was stirred for 15 minutes at -78° C. before 1,1,1,3-tetrafluoroacetone (2.96 mL of a 40% diethyl ether solution) was added. The reaction mixture was kept at -78° C. for five minutes before quenching with 2N hydrochloric acid. Diethyl ether was added and the aqueous layer extracted further with diethyl ether. The combined organic layers were dried, evaporated and the product purified by chromatography, with diethyl ether:chloroform (1:9) as eluent. This yielded the title compound as a white solid (1.64 g) mp 119-120.8; (300 MHz) (CDCl3): 3.77 (s,1, OH), 4.55-4.79 (m,2, CH2F), 7.48-7.61 (m,5, Ar), 7.86-7.94 (m,4, Ar); MS: m/z=373 (M+1). Analysis for C17H12F4O3S: Calculated: C, 54.84; H, 3.25; Found: C, 54.70; H, 3.37.

Aufarbeitung

  1. additionwas added
  2. custombefore quenching with 2N hydrochloric acid
  3. additionDiethyl ether was added
  4. extractionthe aqueous layer extracted further with diethyl ether
  5. customThe combined organic layers were dried
  6. customevaporated
  7. customthe product purified by chromatography, with diethyl ether:chloroform (1:9) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-a48ca5ea368f4fa3a151e6b6aa9489bf
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411973

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