Hydrochloric Acid → 7-Hydroxybenzo[b]thiophene-4-carbaldehyde

HRID 2060877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060877
C[O:2][C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6]([CH:12]=[O:13])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].Cl.C(N(C(S)C)CC)C.Cl>CN(C=O)C>[OH:2][C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6]([CH:12]=[O:13])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 106792907-Methoxybenzo[b]thiophene-4-carbaldehydeHCID 236176041-(Diethylamino)ethanethiol;hydrochlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 594013507-Hydroxybenzo[b]thiophene-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7-Methoxybenzo[b]thiophene-4-carbaldehyde (Preparation 68) (844 mg, 4.39 mmol) was added to a suspension of potassium tert-butoxide (1.5 g, 14.0 mmol) and diethylaminoethanethiol hydrochloride (1.12 g, 6.58 mmol) in DMF (22 mL). The mixture was refluxed for 1 h. After cooling the mixture was acidified to pH 1 with 1N HCl and the aqueous phase extracted with EtOAc. The organic phase was washed with water, brine and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=2.59 min; m/z (ES+)=178.2 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureAfter cooling the mixture
  3. extractionthe aqueous phase extracted with EtOAc
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1707446d7d3440a5860aacb6ff1b041d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278442B2

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