tert-Butanol → butyl (E) 3-(4-iodophenyl)-but-2-enoate

HRID 77346

Reaktionsgleichung

Reaktionsgleichung von HRID 77346
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])(C)C)=[O:11])(OCC)=O)C.[CH3:17][C:18](O)(C)C.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][CH:26]=1)=O>C1COCC1>[I:31][C:28]1[CH:29]=[CH:30][C:25](/[C:23](/[CH3:22])=[CH:9]/[C:10]([O:12][CH2:13][CH2:16][CH2:17][CH3:18])=[O:11])=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 6386tert-ButanolHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 2773685tert-Butyl diethylphosphonoacetate

Produkt 1

HCID 131731881butyl (E) 3-(4-iodophenyl)-but-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of tert-butyl diethylphosphonoacetate (10.0 g, 39.6 mmol) in 30 mL of dry THF was added slowly to a freshly prepared solution of 19 mL of 2.5 M (hexanes) lithium tert-butoxide and tBuOH (30 mL) and stirred for 1 h. A solution of 4-iodoacetophenone (1b) (9.0 g, 36.6 mmol) in 20 mL of dry THF was added to the reaction mixture and stirring was continued overnight. The solvents were removed under vacuum. The residue was dissolved in 400 mL of Et2O and was washed with water (2×30 mL) followed by brine (30 mL) and dried over MgSO4. After filtration and evaporation of the solvent, the crude product was then purified by silica gel column chromatography, eluting with 1% EtOAc in hexane. The product 2b was obtained as an oil (10.0 g, 79% yield). 1HNMR (CDCl3, 300 MHz) δ 1.515 (s, 9H), 2.48 (s, 3H), 6.03 (s, 1H), 7.18 (d, 2H, J=8.4 Hz), 7.68 (d, 2H, J=8.4 Hz). 13C NMR (CDCl3, 75.0 MHz) δ 17.5, 28.3, 80.2, 94.6, 119.5, 128.0, 137.6, 141.9, 152.6, 166.1. Anal. Calcd. for C14H17IO2: C, 48.85; H, 4.98; I, 36.87; 0, 9.3 : Found C, 49.40; H, 5.00, I, 35.97. HRMS (M+H) calc, 345.0351; found, 345.0319.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe solvents were removed under vacuum
  4. dissolutionThe residue was dissolved in 400 mL of Et2O
  5. washwas washed with water (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration and evaporation of the solvent
  8. customthe crude product was then purified by silica gel column chromatography
  9. washeluting with 1% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-1722b2cd6ef24340b156edf76241621a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841257B2

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