Indole-3-Acetic Acid → Ethyl 4-(3-indolyl)-3-oxobutyrate

HRID 583406Notes

Reaction equation

HRID 583406 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]([OH:25])=O)=[CH:14]1.[O:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH2:27]([O:26][C:30](=[O:2])[CH2:29][C:23](=[O:25])[CH2:22][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13][CH:14]=1)[CH3:28]

Participants

4

Reactant 3

HCID 802Indole-3-Acetic AcidHCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 18995239Ethyl 4-(3-indolyl)-3-oxobutyrate

Conditions

Temperature
0 °C

Procedure

24.95 g (154 mmol) of carbonyldiimidazole are added at 0° C. to a solution of 24.5 g (140 mmol) of 3-indolyl-acetic acid in 250 ml of tetrahydrofuran and the mixture is stirred at 0° C. for 30 minutes. 46 g (161 mmol) of bis-(malonic acid monoethyl ester)magnesium salt are then added and the mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated by evaporation, and ice-cold 6N hydrochloric acid is added; diethyl ether is added and the organic phase is separated off. The organic phase is washed with aqueous 10% sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated by evaporation. The title compound is obtained in the form of an orange oil. 1H-NMR (200 MHz): 8.22 (br. s, 1H), 7.53 (d, 1H), 7.37 (d, 1H), 7.28-7.10 (m, 3H), 4.23 (q, 2H), 3,93 (s, 2H), 3.46 (s, 2H), 1.22 (t, 3H).

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hours
  2. concentrationThe reaction mixture is concentrated by evaporation, and ice-cold 6N hydrochloric acid
  3. additionis added
  4. additiondiethyl ether is added
  5. customthe organic phase is separated off
  6. washThe organic phase is washed with aqueous 10% sodium hydrogen carbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c891ab0a679c4ac39709fe626e1e31eb
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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