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Hydrochloric Acid → 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

HRID 1631896
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1631896
[CH3:1][O:2][C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17].C([N-]C(C)C)(C)C.[Li+].[CH3:26][O:27][CH:28]1[CH2:33][CH2:32][CH:31]([CH:34]=[O:35])[CH2:30][CH2:29]1.Cl>O1CCCC1.O>[OH:35][CH:34]([CH:31]1[CH2:32][CH2:33][CH:28]([O:27][CH3:26])[CH2:29][CH2:30]1)[CH:6]1[C:5](=[O:8])[C:4]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])=[C:3]([O:2][CH3:1])[CH2:7]1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 2979194-Methoxycyclohexane-1-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

Produkt 1

HCID 668669535-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (2 g, 8.7 mmol) in dry tetrahydrofuran (25 ml) at −78° C. is added a solution of lithium diisopropylamide (5.8 ml, 10.4 mmol, 1.8 M in hexane/THF/ethylbenzene) dropwise over 20 minutes. The resultant solution is stirred for 30 minutes at −78° C. before adding 4-methoxy-cyclohexanecarbaldehyde (1.4 g, 9.8 mmol) dissolved in tetrahydrofuran (15 ml). The reaction mixture is allowed to warm to room temperature overnight then diluted with water, acidified with 2 N HCl and extracted with ethyl acetate (3×15 ml). The combined organic extract are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give an brown oil. The residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. extractionThe combined organic extract
  3. dry with materialare dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an brown oil
  7. customThe residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g)

Quellen und Nachweise

ORD-Eintrag
ord-266e89607b93468694c448d05d8508de
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791303B2

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