Oxalyl chloride → 3-(2-Hydroxyethyl)-4,6-dimethylindole

HRID 1531963Notes

Reaction equation

HRID 1531963 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:12](Cl)(=O)[C:13](Cl)=[O:14]>CCOCC>[OH:14][CH2:13][CH2:12][C:4]1[C:3]2[C:7](=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=2[CH3:1])[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 98339914,6-dimethyl-1H-indole

Product 1

HCID 222473203-(2-Hydroxyethyl)-4,6-dimethylindoleYield 37.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4,6-Dimethylindole (130 g) was dissolved in Et2O (130 ml), and oxalyl chloride (23.0 g) was dropwise added at 0° C. The mixture was stirred at room temperature for 5 hr, and Et2O was evaporated under reduced pressure. EtOH (200 ml) was added to the residue and the mixture was stirred at room temperature for 15 hr. EtOH was evaporated under reduced pressure. The residue was dissolved in CHCl3 (200 ml). After washing with water, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The obtained residue was added to a suspension of LiAlH4 (17.0 g) in Et2O (200 ml), which was followed by refluxing for 2 hr. The reaction mixture was poured into ice water and extracted with AcOEt (200 ml). The AcOEt layer was washed with water and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1) to give 13.0 g of 3-(2-hydroxyethyl)-4,6-dimethylindole.

Workup

  1. customEt2O was evaporated under reduced pressure
  2. additionEtOH (200 ml) was added to the residue
  3. stirringthe mixture was stirred at room temperature for 15 hr
  4. customEtOH was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in CHCl3 (200 ml)
  6. washAfter washing with water
  7. dry with materialthe mixture was dried over anhydrous sodium sulfate
  8. customCHCl3 was evaporated under reduced pressure
  9. additionThe obtained residue was added to a suspension of LiAlH4 (17.0 g) in Et2O (200 ml), which
  10. temperatureby refluxing for 2 hr
  11. additionThe reaction mixture was poured into ice water
  12. extractionextracted with AcOEt (200 ml)
  13. washThe AcOEt layer was washed with water
  14. dry with materialdried over anhydrous sodium sulfate
  15. customAcOEt was evaporated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1)

Sources & evidence

ORD record
ord-077b50ed01f243418ae38e4326cf8fac
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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