Sodium Sulfate → 2-(2,5-Dimethylpyrrol-1-yl)-1-propanol

HRID 224654Notes

Reaction equation

HRID 224654 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]([CH:14]([CH3:20])[C:15](OCC)=[O:16])[C:10]([CH3:13])=[CH:11][CH:12]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:7][C:8]1[N:9]([CH:14]([CH3:20])[CH2:15][OH:16])[C:10]([CH3:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 12603252Ethyl 2-(2,5-dimethylpyrrol-1-yl)propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 126032532-(2,5-Dimethylpyrrol-1-yl)-1-propanolYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (3.1 g; 80.5 mmoles) was added to 100 ml of dry ether, and an ether solution (50 ml) of 17.9 g (91.8 mmoles) of ethyl 2-(2,5-dimethylpyrrol-1-yl)propionate was gradually added dropwise to the mixture. After the addition, the mixture was heated under reflux for 2 hours, and worked up with a saturated aqueous solution of sodium sulfate. The ethereal layer was concentrated under reduced pressure to afford 13.5 g of crude 2-(2,5-dimethylpyrrol-1-yl)-1-propanol. Acetic anhydride (50 ml) and 50 ml of pyridine were added to the product, and the mixture was allowed to stand at room temperature for 20 hours. It was then concentrated under reduced pressure and then distilled under reduced pressure to afford 2-(2,5-dimethylpyrrol-1-yl)propyl acetate (13.0 g, 66.8 mmoles, 75.7%) having a boiling point of 116°-118° C./6 mmHg.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. concentrationThe ethereal layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e97d677860174f55942235881d1fb56a
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

Loading…