Potassium Carbonate → HCID 19431738, compound

HRID 1077417Notes

Reaction equation

HRID 1077417 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[OH:6][C:7]1[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[OH:5][CH2:4][CH2:3][CH2:2][O:6][C:7]1[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 19217Benzo(b)thiophen-4-ol

Product 1

HCID 19431738HCID 19431738, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-Bromo-1-propanol (1.67 g) was added to a stirred solution of 4-hydroxybenzo[b]thiophene (1.50 g) and potassium carbonate (3.04 g) in 2-butanone (40 ml) under an atmosphere of nitrogen and the mixture was heated under reflux for 3 hours. The mixture was filtered and the filtrate evaporated to dryness. The solid residue was recrystallised from ethanol to give 4-(3-hydroxypropyloxy)benzo[b]thiophene of m.p. 82° C. A solution of N-chloroacetylpyrrolidine (1.47 g) in tetrahydrofuran (THF, 10 ml) was added in one portion to a stirred solution of 4-(3-hydroxypropyloxy)benzo[b]thiophene (1.75 g) and sodium hydride (60% suspension, 0.40 g) in tetrahydrofuran under an atmosphere of nitrogen and stirring was continued for 1 hour at room temperature. The solution was filtered and the filtrate evaporated to afford an oil, which was purified by flash chromatography (silica, ethylacetate:petroleum, 1:1 v/v) to yield the pyrrolidine amide of 3-(4-benzothiophenoxy)propyloxy acetic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customThe solid residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-a5b0afc277d74015a079260fb7606436
Source dataset
uspto-grants-1996_08
Patent number
US05543422

Reaction notes

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