Diethyl Carbonate → Ethyl benzo[b]thiophene-7-carboxylate

HRID 605952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605952
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Mg].[C:12](=O)([O:16]CC)[O:13][CH2:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[CH2:14]([O:13][C:12]([C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 120455387-Bromobenzo[b]thiophene

Produkt 1

HCID 49758023Ethyl benzo[b]thiophene-7-carboxylateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-bromobenzo[b]thiophene (500 mg, 2.36 mmol) is dissolved in dry THF (5.0 mL) under nitrogen. Magnesium turnings (530 mg, 2.83 mmol, 1.20 equiv.) are added and the resulting mixture is heated at reflux until dissolution of the magnesium has occurred. The resulting cloudy yellow solution is allowed to cool to rt and diethyl carbonate (2 mL, excess) is added and stirring continued for one hour, when ammonium chloride (10% aq) is added. The resulting mixture is partitioned between DCM and water and the aqueous layer is extracted with DCM. The organic fractions are combined, washed with brine, dried over Na2SO4 and adsorbed onto silica. Purification by LC using 8/2 cyclohexane/dichloromethane as the eluent afforded the title compound as a pale orange oil (346.2 mg, 71%).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. customThe resulting mixture is partitioned between DCM and water
  3. extractionthe aqueous layer is extracted with DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customPurification by LC

Quellen und Nachweise

ORD-Eintrag
ord-22bb57e40fff46cd9899190912f0b520
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915256B2

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