Hydrochloric Acid → HCID 15725041, compound

HRID 846674Notes

Reaction equation

HRID 846674 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[S:11][C:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[C:13](OCC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[S:11][C:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15724982HCID 15724982, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15725041HCID 15725041, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (20 ml) of ethyl 2-(1-methylindol-2-yl)thio-2-phenylpropionate (3 g) in anhydrous tetrahydrofuran was added dropwise to a suspension (75 ml) of lithium aluminum hydride (670 mg) in anhydrous tetrahydrofuran, and the mixture was heated and refluxed for 2 hours. The reaction solution was allowed to cool, and was poured into ice water. The mixture was acidified by adding 6N hydrochloric acid, and was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was recrystallized from ligroin to give 1.84 g (yield: 70 %) of the product compound as a pale yellow powder. The melting point was 118°-119° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 2 hours
  3. temperatureto cool
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe resulting residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-de160de24ce14e7f8b738ddf8881d492
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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