Water → HCID 53969954, compound

HRID 1292254Notes

Reaction equation

HRID 1292254 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]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=[O:15].[H-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][CH:21]=1.O>CN(C=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:15][C:14](=[O:16])[CH2:13][C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:8]([CH2:26][C:23]3[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][CH:24]=3)[C:7]=2[CH3:12])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 761515-Methoxy-2-methylindole-3-acetic acid

Product 1

HCID 53969954HCID 53969954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxy-2-methyl-3-indoleacetic acid (4 g, 18.3 mmol) in anhydrous DMF (20 mL) at 0°-5° C. was added NaH (1.6 g, 60% dispersion in oil, 40 mmol) and stirred at room temperature for 40 min., then cooled again to 0°-5° C., and treated with 4-chlorophenylmethyl chloride (5.9 g, 36.6 mmol) and let stand at room temperature overnight. Water (50 ml) was added and the mixture was extracted with ethylacetate (100 mL), washed with brine and dried (MgSO4), evaporated in vacuo, and purified by chromatography (silica gel, 10% ethylacetate in pentane) to yield 1-(4-chlorophenylmethyl)-5-methoxy-2-methyl-3-indoleacetic acid 4-chlorophenylmethyl ester.

Workup

  1. temperaturecooled again to 0°-5° C.
  2. waitlet stand at room temperature overnight
  3. extractionthe mixture was extracted with ethylacetate (100 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. custompurified by chromatography (silica gel, 10% ethylacetate in pentane)

Sources & evidence

ORD record
ord-eccb0f9090e749e68aff71ba4fc6bdf8
Source dataset
uspto-grants-1998_05
Patent number
US05756531

Reaction notes

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