Acetone → Ethyl 6-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

HRID 255507Notes

Reaction equation

HRID 255507 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C([O-])([O-])=O.[K+].[K+].CC(C)=O>[Cl-].[Na+].O>[CH2:18]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18459473HCID 18459473, compound

Product 1

HCID 13203761Ethyl 6-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°.

Workup

  1. temperatureOn cooling the mixture
  2. extractionextracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether
  7. customto yield a yellow solid which
  8. customwas dried in vacuo, 4 g, 72%, mp 89°-91°

Sources & evidence

ORD record
ord-f734b12ab828442bb6c58dbc36ee71c8
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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