Ethanol → HCID 640311, compound

HRID 1877783Notes

Reaction equation

HRID 1877783 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[NH:6][CH:7]=1)=[CH2:2].[CH2:12](O)C>[Pd]>[CH3:8][CH2:5][CH2:4][CH:3]([CH3:7])[CH3:1].[C:8]([O:10][CH2:11][CH3:12])(=[O:9])[CH3:5].[CH2:1]([C:3]1[CH:4]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[NH:6][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 18784613Methyl 4-ethenyl-1H-pyrrole-2-carboxylate

Product 2

HCID 640311HCID 640311, compoundHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Charge to a 500 mL Parr bottle, a mixture of 5% palladium on charcoal (0.2 g) in ethanol (25 mL) and add methyl 4-ethenyl-1H-pyrrole-2-carboxylate (1.4 g, 9.3 mmoles). Hydrogenate at 206.8 kPa for 3 h to give complete conversion by LC-MS. Filter through celite and evaporate to give an oil. Pass through a silica gel pad with iso-hexane/ethyl acetate (100:0 to 75:25) to give the title compound as a pale yellow oil (1.12 g). 1H-NMR (CDCl3), δ: 8.87 (1H, br. s), 6.73-6.78 (2H, m), 3.83 (3H, s), 2.50 (2H, q, J=7.8 Hz) and 1.19 (3H, t, J=7.3 Hz).

Workup

  1. additionCharge to a 500 mL Parr bottle
  2. customHydrogenate at 206.8 kPa for 3 h to give complete conversion by LC-MS
  3. filtrationFilter through celite
  4. customevaporate
  5. customto give an oil

Sources & evidence

ORD record
ord-36b8d20ebda94d5a9bb14ca5fd58e282
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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