Hydrochloric Acid → Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate

HRID 962767

Reaktionsgleichung

Reaktionsgleichung von HRID 962767
[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[OH:27])[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 19079832Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate

Produkt 1

HCID 19085543Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoateAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate (5.70 g) was dissolved in N,N-dimethylformamide (40 ml). α-bromo-p-xylene (3.72 g) and potassium carbonate (2.57 g) were added to the resultant solution and stirred for 3 hours at room temperature. The reaction mixture was poured into 2N HCl and extracted with ethyl acetate. The resultant extract was sequentially washed with saturated sodium bicarbonate solution and brine, and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), obtaining 2.77 g of ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate (2.77 g) as light brown crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe resultant extract
  3. washwas sequentially washed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-b9e886295b7646c8a317bc6ffb7d90fc
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760040

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