Acetic Anhydride → 4-Acetoxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

HRID 566726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566726
O[C:2]1([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:6][C:5](=[O:7])[CH:4]=[C:3]1[C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1.OC1(C2C=C(C)C=CC=2)CC(=O)C=C1C1C=CN=CC=1.CN(C1C=CC=CN=1)C.[C:50]([O:53]C(=O)C)(=[O:52])[CH3:51]>C(Cl)Cl>[C:50]([O:53][C:3]1([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)[CH2:4][C:5](=[O:7])[CH:6]=[C:2]1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(=[O:52])[CH3:51]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 212664474-Hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-oneHCID 212665484-Hydroxy-4-pyridine-4-yl-3-m-tolyl-cyclopent-2-en-1-one

Produkt 1

HCID 212665564-Acetoxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-4-pyridine-4-yl-3-m-tolyl-cyclopent-2-en-1-one, and it's regioisomer 4-hydroxy-3-pyridine-4-y1-4-m-toly1-cyclopent-2-en-1-one prepared as described in Example 8, Step E (265 mg, 1.0 mmole) in methylene chloride (5 mL) was added dimethylamino pyridine (183 mg, 1.5 mmole) and acetic anhydride (0.12 mL, 1.2 mmole) at r.t. The reaction mixture was stirred at that temperature for 1 hr before quenching the reaction with 1 mL of methanol. Concentration and purification (silica, hexane/ethyl acetate) gave the title compound as the slower eluting isomer. MS (m/z): Calcd. C19H17NO3(M+): 307, found (M+H) +: 308.1.

Aufarbeitung

  1. custombefore quenching
  2. customthe reaction with 1 mL of methanol
  3. concentrationConcentration and purification (silica, hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8ad9a94d686d46bdb219eae6e7d60c80
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174901B1

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