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Methyl 2,4,5-trimethylphenylacetate → 4-Hydroxy-8-methoxy-3-(2,4,5-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one

HRID 2035301
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2035301
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].C(O[C:18]([C:20]1([OH:28])[CH2:25][CH2:24][N:23]([O:26][CH3:27])[CH2:22][CH2:21]1)=[O:19])C.CC(C)([O-])C.[K+]>C1COCC1>[OH:19][C:18]1[C:20]2([CH2:21][CH2:22][N:23]([O:26][CH3:27])[CH2:24][CH2:25]2)[O:28][C:3](=[O:2])[C:4]=1[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13]
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Komponenten

5

Edukt 3

HCID 22336857Methyl 2,4,5-trimethylphenylacetateHCID 23665647Potassium tert-butoxideHCID 595847504-Hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 595847404-Hydroxy-8-methoxy-3-(2,4,5-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of (2,4,5-trimethyl-phenyl)acetic acid methyl ester (0.6 g, 3.12 mmol) and 4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester (0.76 g, 3.74 mmol) in 7 ml anhydrous THF was added a 1 M solution of potassium tert-butoxide (6.9 ml, 8.87 mmol) in THF at room temperature. The suspension obtained was first stirred at room temperature for one hour, and then refluxed under argon for one hour. After cooling to room temperature, the reaction mixture was concentrated, water was added and the mixture acidified with little HCl (37%). The aqueous layer was extracted with dichloromethane, and the combined organic layers were then washed with brine and dried over sodium sulfate. After filtration and concentration under vacuum, the residue was purified by column chromatography (silica gel, ethyl acetate 100%). Yield: 280 mg of 4-hydroxy-8-methoxy-3-(2,4,5-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one (title compound P2.2) as a white solid, mp 199-204° C.

Aufarbeitung

  1. customThe suspension obtained
  2. temperaturerefluxed under argon for one hour
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated
  5. additionwater was added
  6. extractionThe aqueous layer was extracted with dichloromethane
  7. washthe combined organic layers were then washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration and concentration under vacuum
  10. customthe residue was purified by column chromatography (silica gel, ethyl acetate 100%)

Quellen und Nachweise

ORD-Eintrag
ord-7d37b5fd31284de4b0f634898f8bcc6d
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08574607B2

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