Methanol → HCID 23320881, Verbindung

HRID 280626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280626
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](O)=[O:11])=[C:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1.CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 233208915-Bromo-3-ethyl-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 23320881HCID 23320881, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 5-bromo-3-ethylbenzofuran-2-carboxylic acid (1.91 g) in dry tetrahydrofuran (70 ml) at 0° C. under an atmosphere of dry nitrogen was added dropwise borane-tetrahydrofuran complex (25 ml of 1M solution). The solution was stirred at 0° C. for 1 hour and then at room temperature for 24 hours. Methanol was added continuously to decompose the excess borane complex and then the solution was evaporated. The residue was dissolved in ether and the solution was washed with water and dried (Na2SO4). Evaporation of the ether gave a solid which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallised from ethyl acetate/petrol to give 5-bromo-3-ethyl-2-hydroxymethylbenzofuran (1.05 g), m.p. 93°-94°.

Aufarbeitung

  1. waitat room temperature for 24 hours
  2. customthe solution was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the ether
  7. customgave a solid which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform
  10. customgave a solid which
  11. customwas crystallised from ethyl acetate/petrol

Quellen und Nachweise

ORD-Eintrag
ord-405fb51472444c9bb0b6c1a65ea6df1b
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590200

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