3-Chloro-1-propanol → HCID 20246949, compound

HRID 1462340Notes

Reaction equation

HRID 1462340 reaction equation
[CH:1]([C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1)=[O:2].[H-].[Na+].Cl[CH2:11][CH2:12][CH2:13][OH:14]>CN(C=O)C>[OH:14][CH2:13][CH2:12][CH2:11][N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH:1]=[O:2]

Participants

5

Reactant 3

HCID 123133-Chloro-1-propanolHCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 20246949HCID 20246949, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material may be prepared as follows. A solution of 2-formylpyrrole (1.0 g.) and a 50% w/w dispersion of sodium hydride in oil (0.72 g.) in DMF (20 ml.) was treated with 3-chloropropanol (1.03 g.) and the mixture heated at 90° for 18 hours and then evaporated to dryness. The residue was partitioned between water and ether, and the ether phase was dried and evaporated to dryness to give 1-(3-hydroxypropyl)-2-formylpyrrole (1.48 g.) which was used without further purification.

Workup

  1. customThe starting material may be prepared
  2. temperaturethe mixture heated at 90° for 18 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between water and ether
  5. dry with materialthe ether phase was dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-806ddd5d6bfb4c88a057124e42927421
Source dataset
uspto-grants-1984_07
Patent number
US04460584

Reaction notes

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