Isobutanol → 4-Isobutoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 1929036Notes

Reaction equation

HRID 1929036 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([O:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[C:24]([OH:27])[CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:47](O)[CH:48]([CH3:50])[CH3:49]>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[C:24]([O:27][CH2:47][CH:48]([CH3:50])[CH3:49])[CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668415224-Isobutoxy-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (10.2 ml, 65.28 mmol) is slowly added to a solution of 4-Hydroxy-1H-indole-2-carboxylic acid ethyl ester 79 (9.57 g, 46.63 mmol), triphenylphosphine (17.12 g, 65.28 mmol) and isobutanol (5.9 ml, 63.42 mmol) in 100 ml of THF, so that the temperature always remained below 30° C. Stirring is continued for 3 hours and the solvent is then evaporated. The crude mixture is purified by chromatography on silicagel using first cyclohexane as eluent, then increasing amounts of EtOAc (from 5% to 50%).

Workup

  1. customthe solvent is then evaporated
  2. customThe crude mixture is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-8b0517a787874dd9a9eff7a7ae3cf71d
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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