Formaldehyde → Ethyl 2-methylidenebutanoate

HRID 362440

Reaktionsgleichung

Reaktionsgleichung von HRID 362440
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:17]([O-])([O-])=O.[K+].[K+].C=O.O>CCOCC>[CH2:17]=[C:3]([CH2:2][CH3:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoate

Produkt 1

HCID 291416Ethyl 2-methylidenebutanoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5.0 g (0.019 mol) of triethyl 2-phosphonobutyrate, 5.5 g (0.039 mol) of K2CO3, 6.2 g (0.076 mol) of 37% aqueous formaldehyde solution, and 15 mL of water was heated to about 80° C. for about 45 min. After cooling to RT, 75 mL of ether was added and the organic layer was separated, washed with brine (1×20 mL), dried (MgSO4), and filtered. The ether was carefully removed by distillation, leaving behind 2.1 g (87%) of the title compound as a clear oil which was used directly without further purification. 1H NMR (CDCl3): 67 1.01 (3H, t, J=7), 1.24 (3H, t, J=7), 2.26 (2H, q, J=7), 4.14 (2H, q, J=7), 5.45 (1H, s), 6.06 (1H, s).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe organic layer was separated
  3. washwashed with brine (1×20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe ether was carefully removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-b86d1ac0d50847d384b8902fb40aaab5
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869511

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