Triethylamine → 2-Acetyl-4,5-dihydro-6,8-dimethylnaphtho[1,2-b]thiophene

HRID 131648

Reaktionsgleichung

Reaktionsgleichung von HRID 131648
[CH2:1](N(CC)CC)C.O[C:9]1([CH3:17])[CH2:14]S[C:12]([OH:16])([CH3:15])[CH2:11][S:10]1.Cl[C:19]1[C:28]2[C:23](=C[CH:25]=[CH:26][CH:27]=2)C[CH2:21][C:20]=1[CH:29]=O.[OH-].[Na+]>O.C(O)C>[C:12]([C:11]1[S:10][C:9]2[C:17]3[C:27]([CH2:26][CH2:25][C:14]=2[CH:1]=1)=[C:28]([CH3:23])[CH:19]=[C:20]([CH3:29])[CH:21]=3)(=[O:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 621052,5-Dimethyl-2,5-dihydroxy-1,4-dithianeHCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

Produkt 1

HCID 111728952-Acetyl-4,5-dihydro-6,8-dimethylnaphtho[1,2-b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Next, 1.4 mL of triethylamine was added dropwise to a 10 mL ethanol solution of 0.9 g of 2,5-dihydroxy-2,5-dimethyl-1,4-dithiane, and the system was stirred for 30 minutes at room temperature. To this was added at room temperature a 10 mL ethanol solution of the 1-chloro-2-formyl-3,4-dihydronaphthalene obtained previously, and the system was refluxed under heating overnight. After the reaction, reduced-pressure solvent distillation was performed, first water and then 2M a sodium hydroxide aqueous solution were added under ice cooling, and extraction was performed with ethyl acetate. The organic layer was washed first with a saturated ammonium chloride aqueous solution and then with saturated brine, dried with magnesium sulfate, and subjected to reduced-pressure solvent distillation, and the residue was refined by silica gel column chromatography (20% ethyl acetate/hexane) and then recrystallized with ethanol to obtain 1.6 g of 2-acetyl-4,5-dihydro-6,8-dimethylnaphtho[1,2-b]thiophene (Table 6-1) in the form of yellow crystals.

Aufarbeitung

  1. customobtained previously
  2. temperaturethe system was refluxed
  3. temperatureunder heating overnight
  4. customAfter the reaction, reduced-pressure solvent distillation
  5. extractionextraction
  6. washThe organic layer was washed first with a saturated ammonium chloride aqueous solution
  7. dry with materialwith saturated brine, dried with magnesium sulfate
  8. distillationsubjected to reduced-pressure solvent distillation
  9. customrecrystallized with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f3a32e44c6934fc287a29024a0b603c1
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384974B2

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