Ethyl 2-formylcyclopropanecarboxylate → Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

HRID 561879

Reaktionsgleichung

Reaktionsgleichung von HRID 561879
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

4

Edukt 2

HCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 13005707Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 2-formylcyclopropanecarboxylate in methanol (0.7 M) was added at −0° C. sodium borohydride portionwise. The resulting reaction mixture was stirred at 0° C. for 30 min and then at RT for 1.5 h. The reaction was quenched with sat. aq. NH4Cl and then extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, and filtered. Concentrated of the filtrate in vacuo afforded the title compound as a colorless oil.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. waitat RT for 1.5 h
  3. customThe reaction was quenched with sat. aq. NH4Cl
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationConcentrated of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f34373fe7b3049a9afa4148cfd5a6077
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063105B2

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