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Water → 3-((2,4-Dichlorophenyl)hydroxymethyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

HRID 1072831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1072831
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[C:7]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:8]=2[S:9][C:10]=1[CH3:11])=[O:5].[BH4-].[Na+].O>O1CCCC1.CO>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH:4]([OH:5])[C:6]1[C:7]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:8]=2[S:9][C:10]=1[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 223877633-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

Produkt 1

HCID 223878353-((2,4-Dichlorophenyl)hydroxymethyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiopheneAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylbenzo[b]-thiophene (600 mg, 1.58 mmol) was dissolved in a mixed solvent of tetrahydrofuran (10 ml) and methanol (1 ml), and sodium borohydride (72 mg, 1.9 mmol) was added thereto under ice-cooling. The mixture was stirred for 40 min under ice-cooling. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure to give the objective compound (580 mg, 96%) as colorless crystals.

Aufarbeitung

  1. additionwas added
  2. temperatureunder ice-cooling
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af81a4a32690481c8332a717010ccab5
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06911469B2

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