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4-Methylbenzaldehyde → 3-(3-Chlorophenyl)-alpha-(4-methylphenyl)-2,1-benzisoxazole-5-methanol

HRID 1441466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1441466
[Li]CCCC.CCCCCC.Br[C:13]1[CH:14]=[CH:15][C:16]2[C:17]([CH:28]=1)=[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[O:19][N:20]=2.[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([C:18]2[O:19][N:20]=[C:16]3[CH:15]=[CH:14][C:13]([CH:34]([C:33]4[CH:36]=[CH:37][C:30]([CH3:29])=[CH:31][CH:32]=4)[OH:35])=[CH:28][C:17]=23)[CH:26]=[CH:25][CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 77254-MethylbenzaldehydeHCID 8058HexaneHCID 120166705-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazoleHCID 178418339Butyllithium

Produkt 1

HCID 179761013-(3-Chlorophenyl)-alpha-(4-methylphenyl)-2,1-benzisoxazole-5-methanolAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

nBuLi 1.6 M in hexane (0.112 mol) was added dropwise at −70° C. under N2 flow to a mixture of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.097 mol) in THF (300 ml). The mixture was stirred at −70° C. for 15 min. A mixture of 4-methyl-benzaldehyde (0.112 mol) in THF (100 ml) was added dropwise. The mixture was stirred at −70° C. for 30 min, then hydrolized and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (20-45 μm) (eluent: DCM(EtOAc 96/4). The pure fractions were collected and the solvent was evaporated, yielding 13 g (38.3%) of 3-(3-chlorophenyl)-α-(4-methylphenyl)-2,1-benzisoxazole-5-methanol (intermediate 18).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at −70° C. for 30 min
  3. extractionhydrolized and extracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness
  8. customThe residue was purified by column chromatography over silica gel (20-45 μm) (eluent
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7e9957d78fd440c29802b802707c051c
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07655654B2

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