Hydrochloric Acid → Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate

HRID 962768

Reaction equation

HRID 962768 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6].Br[CH2:37][CH2:38][CH2:39][Cl:40].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][O:27][C:26]2[CH:25]=[CH:24][C:4]([C:5]([C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=3)=[O:6])=[CH:3][C:2]=2[O:1][CH2:37][CH2:38][CH2:39][Cl:40])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19085543Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate

Product 1

HCID 19085526Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoateYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy) benzoyl]indol-1-yl}butanoate (2.77 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (30 ml). 1-Bromo-3-chloropropane (1.39 g) and potassium carbonate (0.97 g) were added to the resultant solution and stirred for 6 hours at 60° C. The reaction mixture was poured into 2N HCl and extracted with ethyl acetate. The resultant extract was sequentially washed with saturated sodium bicarbonate solution and brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), obtaining 2.67 g of ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate as a light yellow oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe resultant extract
  3. washwas sequentially washed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c49e09dbb9cf4c169bcb362f5e6dd098
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Linked notes

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