3-Methyl-2-butanol → 4-(1,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2267760Notes

Reaction equation

HRID 2267760 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.[CH3:47][CH:48]([CH3:52])[CH:49](O)[CH3:50]>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[C:24]([O:27][CH:49]([CH3:50])[CH:48]([CH3:52])[CH3:47])[CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 117323-Methyl-2-butanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668415124-(1,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (5.3 ml, 34.1 mmol) is slowly added to a solution of 4-Hydroxy-1H-indole-2-carboxylic acid ethyl ester 79 (5 g, 24.36 mmol), triphenylphosphine (8.95 g, 34.1 mmol) and 3-Methyl-butan-2-ol (3.58 ml, 33.13 mmol) in 50 ml of THF, so that the temperature always remained below 30° C. Stirring is continued for 3 days 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-fc92f0247be74419823beb5154661881
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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