Dimethylformamide → 3-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

HRID 1515027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515027
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN([CH:26]=[O:27])C>C1COCC1>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH:26]=[O:27])=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 669653423-(3,5-Dichlorophenyl)-propionic acid tert-butyl esterHCID 178418400CID 53628100

Produkt 1

HCID 866328253-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,5-dichlorophenyl)-propionic acid tert butyl ester (1 g, 3.6 mmol) in THF (50 mL) at −78° C. was added dropwise s-butyllithium (1.4 M cyclohexanes; 5.7 mL, 2.2 eq). The resulting red-colored homogeneous solution was stirred under nitrogen at −78° C. for 1 h, at which time DMF (560 mL, 2 eq) was added. After 30 minutes, the reaction was quenched with saturated ammonium chloride solution at. The mixture was allowed to reach ambient temperature and the volatiles were removed under reduced pressure. The residue was partitioned between water and ethyl acetate and the combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by chromatography using 20% ethyl acetate/n-heptanes as eluent to give 3-(3,5-dichloro-4-formylphenyl)-propionic acid tert-butyl ester. 1H-NMR (CDCl3, 400 MHz): δ 10.45 (s, 1H), 7.23 (s, 2H), 2.90 (t, J=7.45 Hz, 2H), 2.55 (t, J=7.45 Hz, 2H), 1.35-1.44 (m, 10H).

Aufarbeitung

  1. additionwas added
  2. customthe reaction was quenched with saturated ammonium chloride solution at
  3. customto reach ambient temperature
  4. customthe volatiles were removed under reduced pressure
  5. customThe residue was partitioned between water and ethyl acetate
  6. dry with materialthe combined organic fractions were dried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-055bccab6ac94d60b26c751d1d2042b0
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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