Water → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

HRID 1308

Reaktionsgleichung

Reaktionsgleichung von HRID 1308
[F-].[K+].[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([C:17]3([C:24]#[C:25][Si](C)(C)C)[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]3)[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4]1.O>CN(C)C=O>[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([C:17]3([C:24]#[CH:25])[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]3)[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 522689Potassium FluorideHCID 539837473-(3-Cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one

Produkt 1

HCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of potassium fluoride (900 mg, 15.6 mmol) and 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one (0.3 g, 0.78 mmol) were stirred in dry N,N-dimethylformamide (3 mL) under an argon atmosphere. After 18 h, the solvent was removed in vacuo, the residue was partitioned between water and ethyl acetate, the aqueous layer was extracted twice with ethyl acetate, the combined extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 4:1 hexanes/ethyl acetate provided a clear colorless oil. Anal. (C20H24O3.1/10 H2O) calcd: C 76.45, H 7.76; found: C 76.32, H 7.60.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. extractionthe combined extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 4:1 hexanes/ethyl acetate
  9. customprovided a clear colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-a765bb3f88ef412dab87283ec66e35db
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723681

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