HCID 20746386, compound → HCID 22600912, compound

HRID 2308159Notes

Reaction equation

HRID 2308159 reaction equation
C([N:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:10]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:9]1[C:40]([O:42][CH2:43][CH3:44])=[O:41])C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)(=O)C>[CH2:30]([O:29][C:10]1[C:11]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:8][C:9]=1[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 20746386HCID 20746386, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22600912HCID 22600912, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Into a 1-L autoclave, 121.1 g (0.197 mole) of the diethyl N-benzyl-3,4-didecyloxypyrrole-2, 5-dicarboxylate, 600 ml of acetic acid and 12.0 g of 10% palladium-carbon were put, and the reaction was carried out for 84 hours at 30° C. and a hydrogen pressure of 1.8×106 Pa. After the reaction was completed, the 10% palladium-carbon was removed by filtration, and the filtrate formed was evaporated to dryness. The residue formed was purified by silica gel column chromatography (eluent: toluene/acetic acid=5/1) to obtain 78.3 g of diethyl 3,4-didecyloxypyrrole-2,5-dicarboxylate (yield: 75.8%).

Workup

  1. customthe 10% palladium-carbon was removed by filtration
  2. customthe filtrate formed
  3. customwas evaporated to dryness
  4. customThe residue formed
  5. customwas purified by silica gel column chromatography (eluent: toluene/acetic acid=5/1)

Sources & evidence

ORD record
ord-4482b010187e4d09904d14db91803f33
Source dataset
uspto-grants-2004_12
Patent number
US06835471B2

Reaction notes

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