Methyl acetoacetate → 6-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 356484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356484
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.C([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:33])=[CH:26][CH:25]=1)C1C=CC=CC=1>CCCCCC.C1COCC1>[CH:34]1([C:32]2([CH2:31][CH2:30][C:27]3[CH:26]=[CH:25][C:24]([OH:23])=[CH:29][CH:28]=3)[O:33][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Komponenten

7

Edukt 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187986683-(4-Benzyloxy-phenyl)-1-cyclohexyl-propan-1-oneHCID 178418339Butyllithium

Produkt 1

HCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-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 6 using 11.6 g (99.9 mmol) of methyl acetoacetate, 4.19 g (105 mmol) of NaH (60% dispersion in oil), 64.0 mL (102 mmol) of 1.6M n-butyl lithium in hexane, 16.1 g (49.9 mmol) of 3-(4-benzyloxy-phenyl)-1-cyclohexyl-propan-1-one (prepared in Example G) and 550 mL of THF. After addition of the ketone, the reaction was stirred for 120 minutes at 0° C., then 1 hour at room temperature. The reaction was quenched with acetic acid (12 mL) and worked up in the usual manner. The crude product was carried on without further purification.

Aufarbeitung

  1. custom1 hour
  2. customat room temperature
  3. customThe reaction was quenched with acetic acid (12 mL)
  4. customThe crude product was carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ef2114e12edf44108a61db48c5ccb6a6
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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