Acetic Anhydride → 4-Acetoxyindole

HRID 257612

Reaktionsgleichung

Reaktionsgleichung von HRID 257612
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12](OC(=O)C)(=[O:14])[CH3:13].[CH2:19](N(CC)CC)C.CN(C1C=CC=CN=1)C>C(OCC)(=O)C>[C:12]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[CH:1]=[CH:19][NH:8]2)(=[O:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 795792-Methyl-3-nitrophenol

Produkt 1

HCID 5839344-AcetoxyindoleAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 3.24 g of trans-6-benzyloxy-2-nitro-β-pyrrolindino -styrene (prepared from 2-methyl-3-nitrophenol by a procedure reported in Organic Synthesis, Coll. Vol. 7, 34, 1990) and 648 mg of 10% pd/C catalyst in 30 ml of ethyl acetate was shaken under hydrogen atmosphere and at 50 psi, for 5 hours. To this reaction mixture were added acetic anhydride (1.4 ml), triethylamine (2.1 ml) and dimethylaminopyridine (324 mg). The resultant mixture was stirred for 1 hour at room temperature. The catalyst was removed over a layer of Celite and the filtrate was evaporated under reduced pressure to give an oily residue to which crushed ice was added. The resulting white precipitate was collected by filtration to give 1.2 g (69% yield) of 4-acetoxyindole: mp 97°-98° C.; HNMR (300 MHz, DMSO-d6)δ 2.32 (s,3H), 6.31 (s,1H), 6.71 (d,1H,J=8Hz), 7.05 (t, 1H, J=8 Hz), 7.28 (d,1H,J=8Hz), 7.32 (s,1H), 11.27 (s,1H).

Aufarbeitung

  1. customreported in Organic Synthesis, Coll
  2. customThe catalyst was removed over a layer of Celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customto give an oily residue to which
  5. customcrushed ice
  6. additionwas added
  7. filtrationThe resulting white precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-07e019f75fe8404dba3239c30da0f5e3
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262546

Verknüpfte Notizen

Wird geladen…