Water → HCID 19939319, Verbindung

HRID 35887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35887
[F:1][C:2]([F:24])([F:23])[C:3]([OH:22])([CH3:21])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:24][C:2]([F:1])([F:23])[C:3]([OH:22])([CH3:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:13])=[O:14])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 199393154,4,4-Trifluoro-3-hydroxy-3-methyl-1-[4-(pyrid-4-ylsulfonyl)phenyl]but-1-yneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19939319HCID 19939319, VerbindungAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4,4,4-trifluoro-3-hydroxy-3-methyl-1-[4-(pyrid-4-ylsulfonyl)phenyl]but-1-yne (0.32 g, 0.90 mmol) in dry tetrahydrofuran (5 mL) was added lithium aluminum hydride (44.4 mg, 1.17 mmol) portionwise over 1 minute and the suspension was stirred for 1 hour. The crude reaction mixture was treated sequentially with water (0.4 mL), 2N sodium hydroxide (0.4 mL), and water (1 mL). This mixture was stirred for 10 minutes, filtered through diatomaceous earth with ethyl acetate. The combined washings and filtrate were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were dried and evaporated. The crude oil was purified by chromatography with ethyl acetate:dichloromethane as the eluent (1:5) to yield the title compound as a white solid (60 mg, 18%); mp 168°-171° C.; NMR (CDCl3): 1.59 (s,3, CH3), 2.43 (s,1, OH), 6.41 (d,1, J=15.9, vinylic), 6.93 (d,1, J=15.9, vinylic), 7.56 (d,2, J=5.9, Ar), 7.76 (d,2, J=5.9, Ar), 7.93 (d,2, J=8.3, Ar), 8.82 (d,2, J=5.9, Ar); MS (EI): m/z=357(M+). Analysis for C16H14F3NO3S: Calculated: C, 53.77; H, 3.95; N, 3.92; Found: C, 53.41; H, 4.05; N, 3.84.

Aufarbeitung

  1. customThe crude reaction mixture
  2. stirringThis mixture was stirred for 10 minutes
  3. filtrationfiltered through diatomaceous earth with ethyl acetate
  4. customThe combined washings and filtrate were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. customThe organic extracts were dried
  7. customevaporated
  8. customThe crude oil was purified by chromatography with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9a6f719b8a5041189216d1e45e201a2b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411973

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