1,1-Dimethoxyethyl(dimethyl)amine → methyl E-4-[5-[5-(dimethylamino)-5-oxopent-1-enyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330198Notes

Reaction equation

HRID 330198 reaction equation
O[CH:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29])[CH:3]=[CH2:4].CO[C:32]([O:37]C)([N:34]([CH3:36])[CH3:35])[CH3:33]>C1(C)C=CC=CC=1>[CH3:36][N:34]([CH3:35])[C:32](=[O:37])[CH2:33][CH2:4]/[CH:3]=[CH:2]/[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 19870651Methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 19870570methyl E-4-[5-[5-(dimethylamino)-5-oxopent-1-enyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoateYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.8 g), N,N-dimethylacetamide dimethyl acetal (0.542 g, redistilled) in dry toluene (20 ml) was stirred and heated under reflux, under an atmosphere of nitrogen for 5 hr. The cooled solution was introduced directly onto a column of silica gel and the product purified by flash chromatography, eluting with ethyl acetate, to give methyl E-4-[5-[5-(dimethylamino)-5-oxopent-1-enyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.72 g, 77%) as an oil: partial NMR (250 MHz, DMSO-d6): 0.81(t, 3H, CH2CH3), 1.75(m, 2H, CH2CH3), 2.45(m, 4H, CH2CH2CO), 2.82(s, 3H, NCH3), 2.98(s, 3H, NCH3), 3.83(s, 3H, OCH3), 3.92(s, 3H, OCH3), 4.0(m, 4H, ArCH2Ar', NCH2), 6.2(d of t, 1H, CH2CH=CH), 6.45(d, J=15.8 Hz, 1H, CH2CH=CH).

Workup

  1. temperatureheated
  2. temperatureunder reflux, under an atmosphere of nitrogen for 5 hr
  3. additionThe cooled solution was introduced directly onto a column of silica gel
  4. customthe product purified by flash chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-7db0ae6f3c194461a4b55d94a7ad71db
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…