Methyl acetoacetate → 5,6-Dihydro-4-hydroxy-6-(pentafluorophenyl)-2H-pyran-2-one

HRID 481847

Reaktionsgleichung

Reaktionsgleichung von HRID 481847
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[C:22](C=O)=[C:21]([F:25])[C:20]([F:26])=[C:19]([F:27])[C:18]=1[F:28]>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:22]2[C:21]([F:25])=[C:20]([F:26])[C:19]([F:27])=[C:18]([F:28])[C:17]=2[F:16])[O:7][C:1](=[O:6])[CH:2]=1

Komponenten

7

Edukt 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 69558PentafluorobenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 547216805,6-Dihydro-4-hydroxy-6-(pentafluorophenyl)-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The title compound was prepared as described in General Method 1 using 2.5 mL of methyl acetoacetate, 1.0 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 3.4 mL of pentafluorobenzaldehyde and 75 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 176°-178° C.). 1H NMR (CDCl3) δ2.89 (dd, 1H), 3.15 (dd, 1H), 3.70 (dd, 2H), 6.02 (dd, 1H).

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. customThe crude product was triturated from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-50c699337819497ab83a256ee9d7db3e
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789440

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