Diethyl Ether → 1,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylate

HRID 1361294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361294
C(C1C(C(O)=O)C(=O)CO1)(C)(C)C.[O:14]=[C:15]1[CH2:19][O:18][CH2:17][CH:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[BH4-].[Na+].CCOCC>C(O)(C)C>[OH:14][CH:15]1[CH2:19][O:18][CH2:17][CH:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydride2×HCID 112292044-Oxo-Tetrahydro-Furan-3-Carboxylic Acid Tert-Butyl EsterHCID 66970985HCID 66970985, Verbindung

Produkt 1

HCID 114128161,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylateAusbeute 86,56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The product of Step A, tert-butyl 4-oxotetrahydrofuran-3-carboxylate (0.95 g, 5.10 mmol) was placed in isopropylalcohol (14 mL) at 0-5° C., NaBH4 (77 mg, 2.04 mmol) was added, and stirred for 2 h. NaBH (77 mg, 2.04 mmol) was added again, and stirred at rt for 1 h, NaBH4 (39 mg, 1.02 mmol) was added, and stirred for 30 min. The reaction mixture was treated with Et2O to dilute, washed with brine, and extracted with Et2O twice. The organic layer was collected, extracted with a NaHCO3 aqueous solution, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/3) to give the title compound (0.83 g, 86.56%).

Aufarbeitung

  1. stirringstirred at rt for 1 h
  2. stirringstirred for 30 min
  3. additionto dilute
  4. washwashed with brine
  5. extractionextracted with Et2O twice
  6. customThe organic layer was collected
  7. extractionextracted with a NaHCO3 aqueous solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-acd147be3cf84ec98cf0254f6fb0e604
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879852B2

Notizen zur Reaktion

Wird geladen…