Acetic Acid → 1-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

HRID 1198551

Reaktionsgleichung

Reaktionsgleichung von HRID 1198551
[H-].[Na+].[C:3]([CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)#[N:4].[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br.C(O)(=O)C>O1CCCC1.ClCCl>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][CH2:5][C:3]#[N:4])[CH:12]=[CH:13]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 150540207-(Cyanomethoxy)indoleHCID 191025633-(1,3-Dioxolan-2-yl)benzyl bromide

Produkt 1

HCID 191026031-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

60% Sodium hydride dispersion in mineral oil (90 mg, 2.25 mmol) was added to a stirred, cooled solution of 7-cyanomethoxyindole (Example 1a) (0.32 g., 1.86 mmol) in tetrahydrofuran (8 ml). The dark mixture was stirred for 15 minutes at room temperature then cooled again whilst a solution of 3-(1,3-dioxolan-2-yl)benzyl bromide (0.50 g., 2.06 mmol) in tetrahydrofuran (2 ml) was added. The mixture was stirred at room temperature for 20 hours then treated with glacial acetic acid (130 μl), diluted with dichloromethane, washed with water, dried and evaporated. The residue was chromatographed on silica in ethyl acetate-hexane (1:3).

Aufarbeitung

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 20 hours
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica in ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-482a656edc4e4126845732fd2c629cc9
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281593

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