Sodium borohydride → 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

HRID 643830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643830
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH:7]=[C:6]1[C:11]([O:13][CH3:14])=[O:12])=[O:4].[BH4-].[Na+]>CO>[CH3:14][O:13][C:11]([CH:6]1[CH2:7][CH:8]([OH:10])[CH:9]=[C:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 591654631,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate

Produkt 1

HCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl esterAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a cold solution (−30° C.) of compound 26 (3.18 g, 16.1 mmol) dissolved in MeOH (23 mL), NaBH4 (0.66 g, 17.5 mmol) was added. After nine minutes the excess of NaBH4 was destroyed by adding brine (80 mL). The mixture was concentrated and extracted with ethyl acetate (4×80 mL). The organic phases were dried, filtrated and concentrated and gave the title compound (3.0 g, 92%) as a yellow oil.

Aufarbeitung

  1. customAfter nine minutes the excess of NaBH4 was destroyed
  2. additionby adding brine (80 mL)
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate (4×80 mL)
  5. customThe organic phases were dried
  6. filtrationfiltrated
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-766fa764f74d42e29bf13f48c3178ec6
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700552B2

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