Ammonium Chloride → Methyl 4-[(4E)-5-(5-fluoro-2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate

HRID 1512201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512201
C([Li])CCC.[Br-].[F:7][C:8]1[CH:9]=[CH:10][C:11]([OH:34])=[C:12]([CH:33]=1)[CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:35]([CH:37]([CH2:50][CH2:51][C:52]1[CH:61]=[CH:60][C:55]([C:56]([O:58][CH3:59])=[O:57])=[CH:54][CH:53]=1)[CH2:38][CH2:39][C:40]1[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=1)=O.[Cl-].[NH4+]>CCCCCC.C1COCC1.O.C(OCC)(=O)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([OH:34])=[C:12](/[CH:13]=[CH:35]/[CH:37]([CH2:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:48][CH:49]=2)[CH2:50][CH2:51][C:52]2[CH:61]=[CH:60][C:55]([C:56]([O:58][CH3:59])=[O:57])=[CH:54][CH:53]=2)[CH:33]=1

Komponenten

9

Edukt 4

HCID 25517Ammonium ChlorideHCID 59397497Dimethyl 4,4'-(3-formylpentane-1,5-diyl)dibenzoateHCID 86638793(5-Fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 59397498Methyl 4-[(4E)-5-(5-fluoro-2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

At 0° C., 2.95 ml (7.39 mmol) of a 2.5 M solution of n-butyllithium in hexane are slowly added dropwise to a solution of 1479 mg (3.2 mmol) of (5-fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromide in 40 ml of THF. The reaction mixture is stirred at this temperature for 45 min. At 0° C., 1080 mg (2.64 mmol) of dimethyl 4,4′-(3-formylpentane-1,5-diyl)dibenzoate in 10 ml of THF are metered in slowly. The reaction solution is stirred at 0° C. for 5 h, saturated ammonium chloride solution is then added and the mixture is diluted with water and ethyl acetate. The organic phase is separated off and the aqueous phase is extracted two more times with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered, and the solvent is removed to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 529 mg (1.11 mmol, 42% of theory) of a colorless oil.

Aufarbeitung

  1. customAt 0° C.
  2. stirringThe reaction solution is stirred at 0° C. for 5 h
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted two more times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c28d475bf25b44c99a4c069ca1375302
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217063B2

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