Formic Acid → 1-(4-Fluorophenyl)-2-nitroethanol

HRID 2120008

Reaktionsgleichung

Reaktionsgleichung von HRID 2120008
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(O)=O.CN(C)C=O>CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.[Cl-].[Ru+2].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 112868511-(4-Fluorophenyl)-2-nitroethanone

Produkt 1

HCID 112983621-(4-Fluorophenyl)-2-nitroethanolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11549108HCID 11549108, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A 50 ml Schlenk flask was charged with 1.831 g (10.0 mmol) of 1-(4-fluorophenyl)-2-nitroethanone, 3.35 ml (24.0 mmol) of triethylamine, 2.26 ml (60.0 mmol) of formic acid, 10 ml of dimethylformamide (DMF), and 31.8 mg (0.05 mmol, S/C=200) of RuCl[(S,S)-Tsdpen](p-cymene) under an atmosphere of argon, and stirring was carried out at 30° C. for 16 hours. The reaction solution was poured into water and extracted with ether, and the organic layer was washed with saturated brine and then dried with anhydrous sodium sulfate. After removing the drying agent, the solvent was distilled off, and the oil so obtained was purified by silica gel column chromatography (eluant; n-hexane:ethyl acetate=9:1) to give 1.48 g of optically active 1-(4-fluorophenyl)-2-nitroethanol. 1H-NMR supported it was the target product, and the yield was 80%.

Aufarbeitung

  1. extractionextracted with ether
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customAfter removing the drying agent
  5. distillationthe solvent was distilled off
  6. customthe oil so obtained
  7. customwas purified by silica gel column chromatography (eluant; n-hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-472b8aec64004447963c91e5831c19eb
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686505B2

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