Ethyl Acetate → HCID 117687648, compound

HRID 920872Notes

Reaction equation

HRID 920872 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([CH:10]=[O:11])=[CH:8][NH:9][C:4]2=[CH:3][CH:2]=1.[H-].[Na+].[C:14]1([C:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH:28](Br)[CH3:29])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>C1COCC1.ClCCl>[C:14]1([C:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][N:9]2[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7]([CH:10]=[O:11])=[CH:8]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 117687689HCID 117687689, compound

Product 1

HCID 117687648HCID 117687648, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1.01 g of indole-3-carboxyaldehyde (6.95 mmol) dissolved in 250 mL THF is added 0.28 g of sodium hydride (11 mmol). After heating the reaction to reflux for 3 hours under nitrogen, 5.0 g of 2-(2-triphenylmethoxyethoxy)ethoxy-1-bromo-ethane (11 mmol) is added. The reaction is allowed to reflux for an additional 16 hours, monitoring by TLC (9:1-ethyl acetate:dichloromethane on alumina). Upon complete consumption of the indole-3-carboxyaldehyde, the reaction is quenched via addition of 25 mL MeOH and the solvent is removed via evaporation. The residue is resuspended in 250 mL dichloromethane and washed 3×200 mL saturated NH4CO3, followed by drying over anhydrous Na2SO4. The crude product is purified via column chromatography over alumina, eluting in dichloromethane with an ethyl acetate gradient.

Workup

  1. temperatureAfter heating
  2. customthe reaction
  3. temperatureto reflux for 3 hours under nitrogen
  4. temperatureto reflux for an additional 16 hours
  5. customUpon complete consumption of the indole-3-carboxyaldehyde
  6. customthe reaction is quenched via addition of 25 mL MeOH
  7. customthe solvent is removed via evaporation
  8. washwashed 3×200 mL saturated NH4CO3
  9. dry with materialby drying over anhydrous Na2SO4
  10. customThe crude product is purified via column chromatography over alumina
  11. washeluting in dichloromethane with an ethyl acetate gradient

Sources & evidence

ORD record
ord-4c3e77aedcde4ee5800804f6e3d36007
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

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