Toluene → HCID 18962557, compound

HRID 654396Notes

Reaction equation

HRID 654396 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH2:19][CH3:20])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:23]1(C)C=CC=CC=1.S(OC)(OC)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:9]1[C:17]([O:18][CH2:19][CH3:20])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 18962543HCID 18962543, compound

Product 1

HCID 18962557HCID 18962557, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The 4-benzyloxy-5-ethoxyindole (1.8 g, 0.0067 mole) obtained in Example (1c), 50% caustic soda (8 ml), toluene (5.4 ml) and tetrabutylammonium hydrogen sulphate (180 mg) are successively introduced. The mixture is heated to 60° C. and dimethyl sulphate (1 g) is introduced. The mixture is left at 60° C. for 30 minutes, diluted with water and the two phases are separated. The organic phase is washed with water, dried and the solvent evaporated. A colorless oil of 4-benzyloxy-5-ethoxy-1-methylindole (1.6 g; yield= 95%) is obtained.

Workup

  1. customthe two phases are separated
  2. washThe organic phase is washed with water
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-e5580f38fe37406bb58fbe8423476e24
Source dataset
uspto-grants-1992_07
Patent number
US05131911

Reaction notes

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