Ethyl 5-(1-tritylimidazol-4-yl)-1-pent-2-enoate → 1H-Imidazole-4-pentanoic acid, 1-(triphenylmethyl)-, ethyl ester

HRID 568558Notes

Reaction equation

HRID 568558 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH:27]=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 57141126Ethyl 5-(1-tritylimidazol-4-yl)-1-pent-2-enoate

Product 1

HCID 117118371H-Imidazole-4-pentanoic acid, 1-(triphenylmethyl)-, ethyl esterYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9.20 g of ethyl 5-(1-tritylimidazol-4-yl)-1-pent-2-enoate in 460 ml of anhydrous ethanol is hydrogenated with 1.88 g of 10% palladium on charcoal at atmospheric pressure for 20 min. The catalyst is removed by filtration through celite. Evaporation provides a solid which is recrystallised from hexane to yield 8.64 g of ethyl 5-(1-tritylimidazol-4-yl)-1-pentanoate, m.p. 84°-86°.

Workup

  1. customThe catalyst is removed by filtration through celite
  2. customEvaporation
  3. customprovides a solid which
  4. customis recrystallised from hexane

Sources & evidence

ORD record
ord-f1e62a6f46f54760b13f2a456002dc66
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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