Acetic Acid → 1-Benzyl-1H-pyrrole-3-carbaldehyde

HRID 2080086Notes

Reaction equation

HRID 2080086 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C[O:14][CH:15]1[CH:19]([CH:20]=O)[CH2:18][CH:17](OC)O1.O>C(OCC)(=O)C>[CH2:1]([N:8]1[CH:17]=[CH:18][C:19]([CH:15]=[O:14])=[CH:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7504BenzylamineHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 156784801-Benzyl-1H-pyrrole-3-carbaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Benzylamine (540 mg, 5.00 mmol) and acetic acid (10 mL) were added to 2,5-dimethoxy-tetrahydrofuran-3-carbaldehyde (1 g, 6.25 mmol), and the solution was stirred for 20 minutes at 90° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with an aqueous solution 2N sodium hydroxide once and with water twice, filtered with a glass filter lined with silica gel, the filtrate was evaporated in vacuo, and title compound (800 mg, 4.3 mmol, 68.8%) was obtained as a brown oil.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with an aqueous solution 2N sodium hydroxide once
  3. filtrationwith water twice, filtered with a glass
  4. filtrationfilter
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-90a45093c7314d0ca5a2b41013255559
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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