Triphenylphosphine → 4-(furan-3-ylmethoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 1929071Notes

Reaction equation

HRID 1929071 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][C:49]([CH2:52]O)=[CH:48]1>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:49]1[CH:50]=[CH:51][O:47][CH:48]=1)[CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 204493-FuranmethanolHCID 5462977Diethyl azodicarboxylateHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 668414384-(furan-3-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-3-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 triturated with ether and the white precipitate is filtered off. It contained mainly product. The mother liquor is purified by chromatography (cyclohexane:EtOAc/95:5) and combined with the first precipitate. Yield: 3 g (>100%).

Workup

  1. customthe solvent is then evaporated
  2. customThe crude residue is triturated with ether
  3. filtrationthe white precipitate is filtered off
  4. customThe mother liquor is purified by chromatography (cyclohexane:EtOAc/95:5)

Sources & evidence

ORD record
ord-ea37f5ee77424760bfa24634f71e7cbe
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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