Ethanol → HCID 86760642, compound

HRID 900752Notes

Reaction equation

HRID 900752 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:13])=[C:5]([CH:11]=[O:12])[C:6]=1[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(O)C>C1COCC1.O>[CH:11]([C:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[N:3]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:4]=1[CH3:13])=[O:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 2798463Methyl 4-formyl-2,5-dimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 86760642HCID 86760642, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

Methyl 2,5-dimethyl-4-formyl-pyrrole-3-carboxylate (500 mg) in THF (5 ml) under nitrogen was added to a suspension of sodium hydride (120 mg of 60% oil dispersion) in dry THF (10 ml). When effervescence had ceased the suspension was cooled to 10° C., and benzyl chloroformate (0.437 ml) was added. After stirring at room temperature for 4 h, ethanol (0.5 ml) was added and then the reaction was poured into water. Extraction into ethyl acetate, washing the extracts with brine, drying and evaporation gave the crude product. Purification by chromatography (SiO2/30%-50% ethyl acetate in isohexane) afforded the subtitle compound (0.6 g).

Workup

  1. extractionExtraction into ethyl acetate
  2. washwashing the extracts with brine
  3. customdrying
  4. customevaporation
  5. customgave the crude product
  6. customPurification by chromatography (SiO2/30%-50% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-42f87498b5b249dc91d11bfc87f4a688
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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