Benzenepropanal → 3-Phenylmethyl-7-methoxyindole

HRID 51465

Reaktionsgleichung

Reaktionsgleichung von HRID 51465
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N.[C:12]1([CH2:18][CH2:19][CH:20]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:12]1([CH2:18][C:19]2[C:6]3[C:5](=[C:4]([O:3][CH3:2])[CH:9]=[CH:8][CH:7]=3)[NH:10][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 7707BenzenepropanalHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Produkt 1

HCID 227407383-Phenylmethyl-7-methoxyindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 15 gm (0.086 mol) of 2-methoxyphenylhydrazine hydrochloride and 12 mL (0.09 mol) of 3-phenylpropionaldehyde in 300 mL of toluene was refluxed for 1.5 hours with azeotropic removal of water. The suspension was cooled, evaporated in vacuo and the residue dissolved in 500 mL of dichloromethane and stirred with 9 mL (0.09 mol) of phosphorous trichloride for 18 hours. The solution was poured into ice-water, stirred well, and made basic with sodium bicarbonate. The organic phase was washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient hexane/5-15% ethyl ether to give product, 8.0 gm, 40%, as a viscous oil. 1H NMR (CDCl3) δ: 3.95 (s, 3H), 4.10 (s, 2H), 6.65 (d, 1H), 6.90 (s, 1H), 7.00 (t, 1H), 7.10 (d, 1H), 7.20 (m, 1H), 7.30 (m, 4H), 8.20 (br s, 1H)

Aufarbeitung

  1. temperatureThe suspension was cooled
  2. customevaporated in vacuo
  3. dissolutionthe residue dissolved in 500 mL of dichloromethane
  4. washThe organic phase was washed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a gradient hexane/5-15% ethyl ether
  8. customto give product, 8.0 gm, 40%

Quellen und Nachweise

ORD-Eintrag
ord-e5b31f1a44974878a00a6afaac8c47d2
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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