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3-[2-(4-Difluoromethoxyphenyl)-2-oxo-acetyl]benzaldehyde → 1-(4-Difluoromethoxyphenyl)-2-[3-(1-hydroxybut-2-ynyl)phenyl]ethane-1,2-dione

HRID 30595
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 30595
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[O:12])=[CH:6][CH:5]=1.[C:23]([Mg]Br)#[C:24][CH3:25]>COCCOC.C1COCC1>[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[C:11]([C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]([OH:17])[C:23]#[C:24][CH3:25])[CH:14]=2)=[O:12])=[CH:6][CH:5]=1
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Komponenten

5

Edukt 2

HCID 597903033-[2-(4-Difluoromethoxyphenyl)-2-oxo-acetyl]benzaldehydeHCID 178419101HCID 178419101, Verbindung

Produkt 1

HCID 686488621-(4-Difluoromethoxyphenyl)-2-[3-(1-hydroxybut-2-ynyl)phenyl]ethane-1,2-dioneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Versuchsvorschrift

A stirred solution of 3-[2-(4-difluoromethoxyphenyl)-2-oxo-acetyl]-benzaldehyde (0.1 g, 0.33 mmol) in dry DME at 0° C. under nitrogen was treated over 10 min with 0.5 M 1-propynyl magnesium bromide in THF. The reaction was stirred for 0.5 h, quenched with saturated ammonium chloride, diluted with water and extracted with ethyl acetate. The combined extracts were dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by flash chromatography (20% to 40% ethyl acetate/petroleum ether) gave 1-(4-difluoromethoxyphenyl)-2-[3-(1-hydroxybut-2-ynyl)phenyl]ethane-1,2-dione as a clear oil, 55 mg (49% yield). Using essentially the same procedure described as described in Example 1, step c, and employing 1-(4-difluoromethoxyphenyl)-2-[3-(1-hydroxy-but-2-ynyl)phenyl]-ethane-1,2-dione (0.055 g, 0.16 mmol), the title product was obtained as a slight yellow foam, 0.044 g (69% yield), identified by NMR and mass spectral analyses. MS (ES+): 400 (M+H).

Aufarbeitung

  1. customquenched with saturated ammonium chloride
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the resultant residue by flash chromatography (20% to 40% ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-3db253a134b2421b860ec8bb95540202
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07423158B2

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