Sodium Chloride → 2-[4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane

HRID 263546

Reaktionsgleichung

Reaktionsgleichung von HRID 263546
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[C:16]([C:18]1([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:26]=2)[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)#[N:17].[Cl-].[Na+]>O1CCCC1.O>[C:16]([C:18]1([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:26]=2)[CH2:19][CH2:20][C:21](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[CH2:22][CH2:23]1)#[N:17]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 834132-Trimethylsilyl-1,3-dithianeHCID 9861604SB-200473HCID 178418339Butyllithium

Produkt 1

HCID 107880172-[4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithianeAusbeute 272 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-trimethylsilyl-1,3-dithiane (9.25 mL, 48.7 mmol) in dry tetrahydrofuran (80 mL) at 0° C. under an argon atmosphere was added rapidly n-butyllithium (2.5M in hexanes, 19.2 mL, 48 mmol). After 10 min, the mixture was cooled to -78° C. and a solution of 4- cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (7.53 g, 23 mmol) in tetrahydrofuran (40 mL) was added. After 10 min, aqueous sodium chloride was added, the mixture was allowed to warm to room temperature and was diluted with water. This mixture was combined with the product of three substantially similar reactions conducted on ketone (3.04, 6.01 and 6.1 g, 48.3 mmol total), the combined mixture was extracted three times with methylene chloride, the extract was dried (magnesium sulfate) and evaporated. Purification by flash chromatography, eluting with 10% ethyl acetate/hexanes, provided a white solid (26 g, 87%): m.p. 115°-116° C.

Aufarbeitung

  1. waitAfter 10 min
  2. temperatureto warm to room temperature
  3. extractionthe combined mixture was extracted three times with methylene chloride
  4. dry with materialthe extract was dried (magnesium sulfate)
  5. customevaporated
  6. customPurification by flash chromatography
  7. washeluting with 10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-34b728e52a4045dba646410bdd4c581d
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643946

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