Furfuryl Alcohol → 4-(furan-2-ylmethoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 1929068Notes

Reaction equation

HRID 1929068 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.[O:47]1[CH:51]=[CH:50][CH:49]=[C:48]1[CH2:52]O>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[C:24]([O:27][CH2:52][C:48]1[O:47][CH:51]=[CH:50][CH:49]=1)[CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668419954-(furan-2-ylmethoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (2.1 ml, 13.65 mmol) is slowly added to a solution of 4-hydroxy-1H-indole-2-carboxylic acid ethyl ester 79 (2 g, 9.75 mmol), triphenylphosphine (3.58 g, 13.65 mmol) and furan-2-yl-methanol (1.18 ml, 12.26 mmol) in 10 ml of THF, so that the temperature always remained below 30° C. Stirring is continued for 2 hours and the solvent is then evaporated. The crude residue is purified by chromatography (cyclohexane:EtOAc/95:5).

Workup

  1. customthe solvent is then evaporated
  2. customThe crude residue is purified by chromatography (cyclohexane:EtOAc/95:5)

Sources & evidence

ORD record
ord-1d60d69efccd4239aaf66d48a0fb4f60
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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