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

HRID 357813

Reaktionsgleichung

Reaktionsgleichung von HRID 357813
[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) δ 2.89 (dd, 1 H), 3.15 (dd, 1 H), 3.70 (dd, 2 H), 6.02 (dd, 1 H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3e032f68de824e6ea046a4d2fb67e0a0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840751

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