Hydrochloric Acid → HCID 10806149, compound

HRID 1974561Notes

Reaction equation

HRID 1974561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10705063HCID 10705063, compound

Product 1

HCID 10806149HCID 10806149, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(5-chloroindol-3-yl)butyric acid (1.50 g), benzyl bromide (1.10 g) and potassium carbonate (0.987 in N,N-dimethylformamide (12 ml) was stirred at 25° C. for 4.5 hours. The mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was chromatographed on silica gel (40 g) eluting with a mixture of hexane and ethyl acetate (10:1) to give benzyl 4-(5-chloroindol-3-yl)butyrate (1.40 g) as pale yellow crystals.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of solvent
  5. customthe residue was chromatographed on silica gel (40 g)
  6. washeluting with a mixture of hexane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-032fc6e6aef84ce08cff64aa20f18ef6
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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