Acetic Acid → Methyl 2,3-Dihydro-3-hydroxy-alpha-(phenylmethyl)-2-oxo-1H-indole-3-acetate

HRID 330596

Reaktionsgleichung

Reaktionsgleichung von HRID 330596
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[C:12]1([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([N-]C(C)C)(C)C.[Li+].C(O)(=O)C>O1CCCC1.O.C1(C)C=CC=CC=1>[OH:5][C:4]1([CH:19]([CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:20]([O:22][CH3:23])=[O:21])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 7054IsatinHCID 7643Methyl 3-phenylpropionateHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 14064716Methyl 2,3-Dihydro-3-hydroxy-alpha-(phenylmethyl)-2-oxo-1H-indole-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a cooled (-5° C.) suspension of isatin (8.85 g, 0.0602 mol), and methyl 3-phenylpropionate (9.88 g, 0.0602 mol) in 220 mL of dry tetrahydrofuran under a nitrogen atmosphere was added lithium diisopropylamide (LDA) (75 mL, 0.1275 mol of a 1.72M solution) over a 11/2 hour period. The reaction mixture was stirred at -5° C. for one hour and then poured into a cooled (0° to 5° C.) solution of toluene (140 mL), and acetic acid (30.6 g, 0.51 mol, 300% excess) over a 1/2 hour period under a nitrogen atmosphere. The transfer was completed with a 200 mL water wash.

Aufarbeitung

  1. temperatureTo a cooled
  2. additionpoured into
  3. washwash

Quellen und Nachweise

ORD-Eintrag
ord-d78311325a644dd3898acce07fcc787e
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04897493

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