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Sodium hydride → HCID 21476978, Verbindung

HRID 2293606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2293606
[C:1]([CH2:6][O:7][C:8]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:9]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)=[C:12]1[C:33]([O:35]CC)=[O:34])([O:3]CC)=[O:2].C(COC1C=C(OC)C=CC=1CN1C2C(=CC(O)=CC=2)C(C2C=CC3OCOC=3C=2)=C1C(OCC)=O)(OCC)=O.[H-].[Na+].ICCC>CN(C=O)C>[C:1]([CH2:6][O:7][C:8]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:9]=1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)=[C:12]1[C:33]([OH:35])=[O:34])([OH:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21476971HCID 21476971, VerbindungHCID 21476972Ethyl 1-(2-carboethoxymethoxy-4-methoxybenzyl)-5-hydroxy-3-(3,4-methlenedioxyphenyl)indole-2-carboxylate

Produkt 1

HCID 21476978HCID 21476978, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Ethyl 1-(2-Carboethoxymethoxy-4-methoxybenzyl)-3-(3,4-methlenedioxyphenyl)-5-(prop-1-yloxy)indole-2-carboxylate. To a solution of ethyl 1-(2-carboethoxymethoxy-4-methoxybenzyl)-5-hydroxy-3-(3,4-methylenedioxyphenyl)indole-2-carboxylate (175 mg, 0.30 mmol) in DMF stirred at ice bath temperature under an argon atmosphere was added a slurry of NaH (11 mg of 80% oil dispersion, 0.36 mmol, oil removed by pentane wash) in DMF (1 mL). After 15 min at ice bath temperature, 1-iodopropane (0.255 g, 1.5 mmol) was added and the ice bath was removed. The reaction mixture was stirred an additional 30 min at room temperature then partitioned between 3N HCl (25 mL) and EtOAc (75 mL). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent was removed in vacuo and the resulting solid crystallized from EtOH to afford the title compound (83 mg 47%); m.p. 89°-91° C.

Aufarbeitung

  1. customthe ice bath was removed
  2. customthen partitioned between 3N HCl (25 mL) and EtOAc (75 mL)
  3. extractionThe organic extract
  4. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe resulting solid crystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-2d3b872481914e04ba2687623c54f4d0
Quelldatensatz
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05686481

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