Ethanol → HCID 15023271, compound

HRID 129342Notes

Reaction equation

HRID 129342 reaction equation
C(O)C.O[CH:5]([C:17]1[CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[NH:20][CH:21]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H][H]>[C].[Pd].C(Cl)(Cl)Cl>[CH2:5]([C:17]1[CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[NH:20][CH:21]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 15023260HCID 15023260, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15023271HCID 15023271, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To an ethanol solution (2.0 liters) of 258.0 g (0.73 mol) of methyl 4-(1-hydroxydodecyl)pyrrole-2-carboxylate prepared in Synthetic Example 11 was added 16 g of 10% palladium-carbon. A catalytic reduction with hydrogen was carried out at 50° C. under hydrogen atmosphere. After the reaction was completed within 5.5 hours, 1.5 liters of chloroform was added to the reaction mixture. The catalyst was filtered off, and the solvent was removed under a reduced pressure to give crystals. Recrystallization from 950 ml of ethanol afforded 179.6 g (83% yield) of methyl 4-dodecylpyrrole-2-carboxylate as white crystals, m.p. 68°-69° C.

Workup

  1. customwas carried out at 50° C. under hydrogen atmosphere
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was removed under a reduced pressure
  4. customto give crystals
  5. customRecrystallization from 950 ml of ethanol

Sources & evidence

ORD record
ord-387fa7622a334838809d9bdac7ceba33
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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