2-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester → 2-Acetylamino-5-(1-hydroxy-butyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 1894026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894026
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17](=[O:19])[CH3:18].[CH2:21]([Mg]Cl)[CH2:22][CH3:23]>CCOCC>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]([OH:11])[CH2:21][CH2:22][CH3:23])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17](=[O:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 591644232-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl esterHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 585329282-Acetylamino-5-(1-hydroxy-butyl)-4-trifluoromethyl-benzoic acid methyl esterAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2-acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester (1.52 g, 5.26 mmol) in absolute Et2O (52 mL), under argon, was added a solution of propylmagnesium chloride (2.0 M in Et2O, 5.3 mL, 11 mmol) over 5 min at 20° C. An immediate crystallisation occurred along with an exotherm. The reaction mixture was cooled to 20° C. using an ice/water bath. The reaction mixture was stirred at r.t. for 1 h then poured onto sat. aq NH4Cl and EtOAc. The pH was adjusted to 7 with sat. aq NH4Cl and the layers were separated. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (25 g silica gel, hexanes/EtOAc (1:0→7:3)) to give product as colorless crystals (409 mg, 23%). m.p.: 97-101° C., ESI-MS: m/z 334 [M+H]+, m/z 332 [M−H]−.

Aufarbeitung

  1. customAn immediate crystallisation
  2. additionthen poured onto sat. aq NH4Cl and EtOAc
  3. customthe layers were separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (25 g silica gel, hexanes/EtOAc (1:0→7:3))

Quellen und Nachweise

ORD-Eintrag
ord-a502f22e4fc9453b8afd7c371857dc12
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513268B2

Notizen zur Reaktion

Wird geladen…