Ethyl Acetate → HCID 86745939, compound

HRID 260469Notes

Reaction equation

HRID 260469 reaction equation
CON(C)[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[S:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[C:15]1([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:4]=[S:5])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86745937HCID 86745937, compound

Product 1

HCID 86745939HCID 86745939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Methoxy-N-methyl-3-phenylthioindole-2-carboxamide (1.57 g, 5.26 mmol) was dissolved in tetrahydrofuran (150 mL) and cooled to 0° C. under nitrogen. A solution of lithium aluminum hydride in tetrahydrofuran (5.76 mL, 1M) was added slowly via syringe and the reaction stirred a total of 1.5 h. Ethyl acetate (30 mL) was added, followed by saturated sodium potassium tartrate solution. The layers were separated and the organic phase washed with saturated brine and dried over magnesium sulfate. Filtration and evaporation of solvent gave the title compound as a yellow solid.

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-fd5e9f33dd234681bc80e43ed2c54e42
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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