Ammonium Chloride → tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

HRID 1920593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920593
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([O:36][C:37](=[O:61])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44]([CH:59]=O)[CH2:45][C:46]2[CH:58]=[CH:57][C:49]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)[CH3:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:34]([O:36][C:37](=[O:61])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44](/[CH:59]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][C:46]2[CH:58]=[CH:57][C:49]([C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)[CH3:35]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57965755tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoateHCID 178418339Butyllithium

Produkt 1

HCID 57965746tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

At 0° C., 3.11 ml (7.78 mmol) of a 2.5 M solution of n-butyllithium in hexane are added slowly to a solution of 1.874 g (4.2 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 25 ml of anhydrous THF, and the mixture is stirred for 45 minutes. At this temperature, 1.080 g (2.78 mmol) of tert-butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoate are metered in slowly, and the mixture is stirred at 0° C. for four hours. After complete conversion, saturated ammonium chloride solution is added, and the reaction solution is concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is evaporated to dryness. The crude product obtained is purified by preparative HPLC. This gives 162 mg (8% of theory) of a colorless oil.

Aufarbeitung

  1. stirringis stirred at 0° C. for four hours
  2. concentrationthe reaction solution is concentrated to dryness
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8c704c17c979436e82222cccaa22e96f
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168821B2

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