Neopentyl alcohol → 4-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid methyl ester

HRID 1929061Notes

Reaction equation

HRID 1929061 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([OH:26])[CH:22]=[CH:21][CH:20]=2)=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:46][C:47]([CH3:51])([CH3:50])[CH2:48]O>C1COCC1>[CH3:13][O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([O:26][CH2:46][C:47]([CH3:51])([CH3:50])[CH3:48])[CH:22]=[CH:21][CH:20]=2)=[O:16]

Participants

6

Reactant 4

HCID 6404Neopentyl alcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22310940Methyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668412144-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.414 ml, 2.66 mmol) is slowly added to a solution of 4-Hydroxy-1H-indole-2-carboxylic acid methyl ester 75 (363 mg, 1.9 mmol), triphenylphosphine (698 mg, 2.66 mmol) and 2,2-Dimethyl-propan-1-ol (228 mg, 2.58 mmol) in 8 ml of THF. Stirring is continued for 20 hours and the solvent is then evaporated. The crude mixture is purified by chromatography on silicagel using cyclohexane/EtOAc (9/1).

Workup

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

Sources & evidence

ORD record
ord-8dfceb5b804946feaf6114fa87787f4a
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

Loading…