Sodium borohydride → HCID 21476897, Verbindung

HRID 2293582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293582
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydride2×HCID 21476898HCID 21476898, Verbindung

Produkt 1

HCID 21476897HCID 21476897, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 0.609 g (2.96 mmol) of the product of Step C dissolved in 10 mL of methanol was added 0.056 g (1.48 mmol) of sodium borohydride in small portions as the reaction mixture was stirred at room temperature under a nitrogen atmosphere. After stirring for 30 minutes the excess sodium borohydride was quenched by addition of 10% aqueous NaHSO4. The methanol was removed in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then purified on a silica gel flash chromatography column eluted with 20% EtOAc-hexane; evaporation of the purified fractions and drying in vacuo afforded 0.408 g (66%) of the title compound.

Aufarbeitung

  1. customwas quenched by addition of 10% aqueous NaHSO4
  2. customThe methanol was removed in vacuo
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified on a silica gel flash chromatography column
  9. washeluted with 20% EtOAc-hexane
  10. customevaporation of the purified fractions
  11. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-99d17b48bd9b4aeba03a9d1d2795067d
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686478

Notizen zur Reaktion

Wird geladen…