Dichloromethane → 2-Chloro-3-(4-methoxyphenyl)propanal

HRID 500108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500108
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]=[O:20])=[CH:13][CH:12]=1.ClCCl>N1CCC[C@@H]1C(O)=O>[Cl:1][CH:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)[CH:19]=[O:20]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 111266073-(4-Methoxyphenyl)propanal

Produkt 1

HCID 121027562-Chloro-3-(4-methoxyphenyl)propanalAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8988D-ProlineKatalysator

Versuchsvorschrift

N-Chlorosuccinimide (980 mg, 0.0073 mol) was added to a mixture of 3-(4-methoxyphenyl)propanal (1.0 g, 6.1 mmol) and D-proline (40 mg, 0.3 mmol) in dichloromethane (10 mL, 200 mmol) at 0° C. The reaction mixture was warmed to RT after 1 h, quenched with water, and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes to give the desired product (860 mg). 1H NMR (400 MHz, CDCl3): 9.52 (s, 1H), 7.18 (dd, 2H), 6.84 (dd, 2H), 4.36 (m, 1H), 3.80 (s, 3H), 3.32 (m, 1H), 3.02 (m, 1H).

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9e6a8d100dbb427daa02525f0451b8c6
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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