3-Methylbenzaldehyde → Ethyl 3-methylcinnamate

HRID 1517695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517695
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14](=[O:30])[CH2:15]P(OCC(F)(F)F)(OCC(F)(F)F)=O)[CH3:12].C1OCCOCCOCCOCCOCCOC1.[C:49]1([CH3:57])[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=O)[CH:50]=1>C1COCC1>[CH2:11]([O:13][C:14](=[O:30])[CH:15]=[CH:57][C:49]1[CH:50]=[C:51]([CH3:55])[CH:52]=[CH:53][CH:54]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 121053-MethylbenzaldehydeHCID 2855718-Crown-6HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11759356Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate

Produkt 1

HCID 589327Ethyl 3-methylcinnamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

KHMDS (4.0 g, 20.0 mmol) was added to a solution of ethyl[bis(2,2,2-trifluoro-ethoxy)phosphinyl]acetate (4.7 mL, 20.0 mmol) and 18-crown-6 (10.6 g, 40.0 mmol) in THF (200 mL) at −78° C., and stirred for 30 minutes. m-Tolualdehyde (2.1 mL, 18 mmol) was added and the reaction mixture was stirred for 3 hours from −78° C. to room temperature. The reaction was quenched with aqueous hydrochloric acid (1 M solution, 100 mL), and the product was extracted with EtOAc (3×100 mL). The organic extracts were washed with brine (100 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C12H14O2+H: 191, observed: 191.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 3 hours from −78° C. to room temperature
  2. customThe reaction was quenched with aqueous hydrochloric acid (1 M solution, 100 mL)
  3. extractionthe product was extracted with EtOAc (3×100 mL)
  4. washThe organic extracts were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b69f022a9b6d4f8ca8a0302ee404d34d
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232311B2

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