Acetic Acid → HCID 19697015, compound

HRID 863625Notes

Reaction equation

HRID 863625 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:12][C:13](Cl)=[O:14])=[CH:6]2.C(O)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:12][CH:13]=[O:14])=[CH:6]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 19697021HCID 19697021, compound

Product 1

HCID 19697015HCID 19697015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-methoxy-2-indolylacetyl chloride (0.1 mol.) in dry tetrahydrofuran is treated with 0.25 mole of lithium aluminum tri-t-butoxy hydride with ice-cooling and stirring. After the initial reaction, the mixture is stirred at room temperature for 4 hours and poured into ice. Excess of acetic acid is added, and the product is extracted with ether. The ethereal solution is washed with sodium bicarbonate, dried over sodium sulfate, and evaporated to a syrup. Chromatography of the residue on a column of silica gel, using ether-petroleum ether (v./v.) 10-30% as eluent, gives 5-methoxy-2-indolyl acetaldehyde.

Workup

  1. temperaturecooling
  2. customAfter the initial reaction
  3. stirringthe mixture is stirred at room temperature for 4 hours
  4. additionpoured into ice
  5. extractionthe product is extracted with ether
  6. washThe ethereal solution is washed with sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customevaporated to a syrup

Sources & evidence

ORD record
ord-e1a18865490a48e395e01d57208df313
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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