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

HRID 2120007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120007
[CH3:1][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>[N+:10]([CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:13])([O-:12])=[O:11]

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 2297441-(4-Methylphenyl)-2-nitroethanone

Produkt 1

HCID 114808201-(4-Methylphenyl)-2-nitroethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11549108RuCl[(S,S)-Tsdpen](p-cymene)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A 50 ml Schlenk flask was charged with 1.075 g (6.0 mmol) of 1-(4-methylphenyl)-2-nitroethanone, 2.01 ml (14.4 mmol) of triethylamine, 1.36 ml (36.0 mmol) of formic acid, 6 ml of dimethylformamide (DMF), and 38.2 mg (0.06 mmol, S/C=100) 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 0.60 g of optically active 2-nitro-1-(4-methylphenyl)ethanol.

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-e67b1162ccbc4b869885c837c64e3d65
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686505B2

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