Diethyl Ether → 1-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol

HRID 1785221

Reaktionsgleichung

Reaktionsgleichung von HRID 1785221
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17]=[O:18].C[Mg+].[Br-].[CH2:22](OCC)C>C1COCC1>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=2)[S:4][C:3]=1[CH:17]([OH:18])[CH3:22]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 219865503-Methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehydeHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 219863591-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.130 g, 0.481 mmole) in THF (5 mL), is injected 3.0 M MeMgBr in ethyl ether (0.27 mL, 0.810 mmole) dropwise. The reaction is stirred for 2 hours. The reaction is quenched with saturated NH4Cl(aq) (10 mL), then the aqueous solution is extracted with ethyl acetate (3×15 mL). The combined organic solution is washed with brine (3×50 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 0-20% ethyl acetate in hexane and concentrated to provide the titled compound as yellow solid.

Aufarbeitung

  1. customThe reaction is quenched with saturated NH4Cl(aq) (10 mL)
  2. extractionthe aqueous solution is extracted with ethyl acetate (3×15 mL)
  3. washThe combined organic solution is washed with brine (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is purified on a silica gel column
  7. washeluting with 0-20% ethyl acetate in hexane
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-acb9feedec8c49e6b9950982176e97e0
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504433B2

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