1-Iodonaphthalene → Methyl 4-(1-naphthyl)-2-oxobutyrate

HRID 278471

Reaktionsgleichung

Reaktionsgleichung von HRID 278471
P(CCCC)(CCCC)CCCC.CCN(CC)CC.[OH:21][CH:22]([CH:27]=[CH2:28])[C:23]([O:25][CH3:26])=[O:24].I[C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:38]1([CH2:28][CH2:27][C:22](=[O:21])[C:23]([O:25][CH3:26])=[O:24])[C:39]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:36][CH:37]=1

Komponenten

8

Edukt 4

HCID 70041-IodonaphthaleneHCID 8471TriethylamineHCID 13831TributylphosphineHCID 545123Methyl 2-hydroxybut-3-enoate

Produkt 1

HCID 18370780Methyl 4-(1-naphthyl)-2-oxobutyrateAusbeute 6,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of Pd(OAc)2 (340 mg), nBu3P (613 mg), and Et3N (1.99 g) in DMF (30 ml) was added methyl 2-hydroxy-3-butenoate (1.76 g) followed by 1-iodonaphthalene (5.0 g), and the reaction mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was poured into water (300 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel (130 g) column chromatography eluting with hexane/ethyl acetate (50:1) to give methyl 4-(1-naphthyl)-2-oxobutyrate (254 mg) as a red oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel (130 g) column chromatography
  6. washeluting with hexane/ethyl acetate (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-9e3c425c714a4a85a45538e47de2e0fe
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359145B1

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