Methanol → HCID 20515674, compound

HRID 1902526Notes

Reaction equation

HRID 1902526 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([C:12]=2[CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.[C:20]([O-:25])(=[O:24])[C:21](C)=[CH2:22].[CH3:26]O>O1CCCC1>[C:20]([CH2:21][CH2:22][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:4]1[CH:1]1[CH2:2][CH2:3]1)([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 87595MethacrylateHCID 20515684HCID 20515684, compound

Product 1

HCID 20515674HCID 20515674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-cyclopropyl-3-(3-pyridylmethyl)indole (1.98 g), methacrylate (2.06 g) and "Triton B" in methanol (0.5 ml) in tetrahydrofuran (50 ml) was heated under reflux for 4 hours and then evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with a mixture of chloroform and petrol (b.p. 40°-60°) (3:1) gave 1-(2-carbomethoxyethyl)-2-cyclopropyl-3-(3-pyridylmethyl)indole as an oil (1.20 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washElution
  11. additionwith a mixture of chloroform and petrol (b.p. 40°-60°) (3:1)

Sources & evidence

ORD record
ord-24274900a77d49a4b228fb7b2a8adcb4
Source dataset
uspto-grants-1982_12
Patent number
US04363912

Reaction notes

Loading…