3-Acetylbenzothiophene → 1-(1-Benzothiophen-3-yl)ethan-1-ol

HRID 1837480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837480
[CH3:1][C:2]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:6][CH:5]=1)=[O:3].[BH4-].[Na+]>C(O)C>[OH:3][CH:2]([C:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:6][CH:5]=1)[CH3:1]

Komponenten

4

Edukt 2

HCID 143163-AcetylbenzothiopheneHCID 4311764Sodium borohydride

Produkt 1

HCID 129927691-(1-Benzothiophen-3-yl)ethan-1-olAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 3-acetyl thianaphthene (2.024 g, 11.5 mmol) in ethanol (15 mL) was added sodium borohydride (0.434 g, 11.5 mmol). The mixture was stirred at 20° C. for 4 hours then evaporated, diluted with brine and extracted 3 times with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and evaporated to give the intermediate title compound as a clear oil (1.924 g, 94%) which was used as is in subsequent reactions. FDMS m/e=178 (M+).

Aufarbeitung

  1. customthen evaporated
  2. additiondiluted with brine
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ac322796d8124832b218352dbbf93bff
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784180B2

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