18-Crown-6 → Methyl 3-(3-cyanophenyl)prop-2-enoate

HRID 2184898

Reaktionsgleichung

Reaktionsgleichung von HRID 2184898
P(=O)([O-])O[C:3]([CH2:13][C:14](F)(F)F)(CC(F)(F)F)[C:4]([O:6][CH3:7])=[O:5].C1OCCOCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:48]([C:50]1[CH:51]=C([CH:55]=[CH:56][CH:57]=1)C=O)#[N:49]>C1COCC1.CCOC(C)=O.CCCCCC>[C:48]([C:50]1[CH:51]=[C:14]([CH:55]=[CH:56][CH:57]=1)[CH:13]=[CH:3][C:4]([O:6][CH3:7])=[O:5])#[N:49]

Komponenten

7

Edukt 4

HCID 2855718-Crown-6HCID 90670m-FormylbenzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178500451HCID 178500451, Verbindung

Produkt 1

HCID 53396017Methyl 3-(3-cyanophenyl)prop-2-enoateAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (1.00 g, 3.14 mmol) and 18-crown-6 (4.14 g, 15.7 mmol) in THF (50 mL) at −78 C, potassium bis(trimethylsilyl)amide (6.3 mL, 0.5 M in toluene, 3.15 mmol) was added dropwise. After the addition was completed, 3-cyanobenzaldehyde (0.412 g, 3.14 mmol) in THF (8 mL) was added. The mixture was stirred at −78 C for 30 min before it was quenched with aq. NH4Cl. Water and ether were added. Aqueous phase was separated, extracted with ether once more. The combined organic solutions were dried over Na2SO4, concentrated in vacuo to give a solid, which was purified by a silica gel column, first eluted with EtOAc/hexane (5/95), then with EtOAc/hexane (10/90) to give the titled compound (0.40 g) (yield: 68%). 1H NMR (CDCl3) 7.85 (s, 1H), 7.77 (d, 1H, J=8 Hz), 7.60 (d, 1H, J=8 Hz), 7.45 (t, 1H, J=8 Hz), 6.91 (d, 1H, J=12 Hz), 6.06 (d, 1H, J=12 Hz).

Aufarbeitung

  1. additionAfter the addition
  2. customwas quenched with aq. NH4Cl
  3. additionWater and ether were added
  4. customAqueous phase was separated
  5. extractionextracted with ether once more
  6. dry with materialThe combined organic solutions were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a solid, which
  9. customwas purified by a silica gel column
  10. washfirst eluted with EtOAc/hexane (5/95)

Quellen und Nachweise

ORD-Eintrag
ord-57f5192d728a4a3e8f6b70f7381216e3
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399627B1

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