Water → 2-(1-Hydroxycyclohexyl)-6-methoxybenzothiophene

HRID 1453908

Reaktionsgleichung

Reaktionsgleichung von HRID 1453908
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[CH:6]=1.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CCOCC>[OH:19][C:13]1([C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[CH:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7967CyclohexanoneHCID 235129022-Bromo-6-methoxybenzo[b]thiophene

Produkt 1

HCID 190027692-(1-Hydroxycyclohexyl)-6-methoxybenzothiopheneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To Mg (0.22 g, 9.05 mmol) under argon in Et2O (20 ml) was added dropwise a solution of bromide (4) (2.00 g, 8.23 mmol) in Et2O (20 ml). The mixture was refluxed for 2 h, a solution of cyclohexanone (1.00 ml, 9.87 mmol) in Et2O (5 ml) was added and the mixture was refluxed for 2 h. It was poured into iced water. The solution was extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under vacuum to give 8.00 g as an oil. Triturating from diisopropyl ether afforded 2-(1-hydroxycyclohexyl)-6-methoxybenzothiophene as a white powder (0.90 g, 65%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturethe mixture was refluxed for 2 h
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give 8.00 g as an oil
  8. customTriturating from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-acec88ae341347f69959d4290ba39959
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476691B2

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