Water → HCID 21200954, Verbindung

HRID 363051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363051
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 44129571HCID 44129571, Verbindung

Produkt 1

HCID 21200954HCID 21200954, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 26-3 (0.391 g, 1.75 mmol) in methylene chloride (6 ml) cooled in an ice-bath in a 3-necked round bottom flask equipped with a nitrogen inlet and rubber septum was added 1.0M boron tribromide in methylene chloride (3.9 ml, 3.9 mmol) via syringe. The resulting mixture was stirred 18 h while warming to ambient temperature. Water (7 ml) was added and the mixture was extracted with ether (35 ml). The organic fraction was washed with brine (10 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:5 increasing to 1:3), to give product 26-4 as a white solid, mp: 163°-164° C.

Aufarbeitung

  1. customequipped with a nitrogen inlet
  2. extractionthe mixture was extracted with ether (35 ml)
  3. washThe organic fraction was washed with brine (10 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with ethyl acetate/hexane (1:5 increasing to 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-0942628a91f448e199247feee0023e0b
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872138

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