Oxalyl chloride → 3,5-Bis(trifluoromethyl)phenylmethyl 4-Oxo-1-phenylcyclohexanecarboxylate

HRID 966983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966983
C(Cl)(=O)C(Cl)=O.[O:7]=[C:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH2:35]O)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>CN(C)C=O.C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[O:7]=[C:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:14]([O:16][CH2:35][C:27]2[CH:28]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:30]=[C:25]([C:24]([F:23])([F:37])[F:38])[CH:26]=2)=[O:15])[CH2:10][CH2:9]1

Komponenten

7

Edukt 3

HCID 65578Oxalyl chlorideHCID 1229333,5-Bis(trifluoromethyl)benzyl alcoholHCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acid

Produkt 1

HCID 222935373,5-Bis(trifluoromethyl)phenylmethyl 4-Oxo-1-phenylcyclohexanecarboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (4.8 mL, 55 mmol) was added to a solution of 4-oxo-1-phenylcyclohexanecarboxylic acid (Description 2, 6 g, 27 mmol) and dimethylformamide (1 drop) in toluene (150 mL) and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and toluene was added. The solvent was evaporated under reduced pressure and the residue was dissolved in toluene (100 mL). 3,5-Bis(trifluoromethyl)benzenemethanol (6.25 g, 26 mmol) and 4-dimethylaminopyridine (3.62 g, 30 mmol) were added and the mixture was heated under reflux for 24 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (100 mL) and hydrochloric acid (2M, 100 mL). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/CH2Cl2 (60:40 increasing to 50:50) to give the title compound (4.5 g, 40%). 1H NMR (360 MHz, CDCl3) δ 2.33-2.53 (6H, m), 2.72-2.77 (2H, m), 5.23 (2H, s), 7.28-7.41 (5H, m), 7.51 (2H, s), and 7.77 (1H, s).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure and toluene
  2. additionwas added
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in toluene (100 mL)
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 24 hours
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was partitioned between ethyl acetate (100 mL) and hydrochloric acid (2M, 100 mL)
  9. dry with materialThe organic layer was dried (MgSO4)
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by flash column chromatography on silica gel
  12. washeluting with isohexane/CH2Cl2 (60:40 increasing to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-2291b995879c44cea272841f13ac3372
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953792B2

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