Potassium tert-butoxide → HCID 69099792, Verbindung

HRID 2251534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251534
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[CH2:17][CH2:18][C:19]2[CH:33]=[CH:32][C:22]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=2)=[N:14][CH:15]=1)(=O)[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C(O)(C)(C)C>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:42])([F:44])[F:43])=[CH:37][CH:36]=2)[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:32][CH:33]=2)=[N:14][CH:15]=1)([CH3:1])=[CH2:8]

Komponenten

6

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 59643195HCID 59643195, Verbindung

Produkt 1

HCID 69099792HCID 69099792, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyltriphenylphosphonium bromide (101 mg; 0.28 mmol) in 0.76 ml of THF was treated under nitrogen with potassium tert-butoxide (0.28 ml of a 1M solution in tert-butanol). After 10 minutes, ethyl 2-[4-(2-{(5-acetylpyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (100 mg; 0.19 mmol) was added. After 2 hours the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated. Purification by flash chromatography using 10% ethyl acetate-hexane mixtures afforded ethyl 2-[4-(2-{(5-isopropenylpyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (30 mg; 30% yield).

Aufarbeitung

  1. concentrationAfter 2 hours the reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9c8be63b07474ba3b193410a9cf1da9f
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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