Hydrochloric Acid → 7-(3-Chloro-2-hydroxypropoxy)-2-ethoxycarbonylbenzofuran

HRID 1906434Notes

Reaction equation

HRID 1906434 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[ClH:20]>C(Cl)(Cl)Cl>[Cl:20][CH2:19][CH:2]([OH:1])[CH2:3][O:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 202119967-(2,3-Epoxypropoxy)-2-ethoxycarbonylbenzofuran

Product 1

HCID 138234707-(3-Chloro-2-hydroxypropoxy)-2-ethoxycarbonylbenzofuran

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

There was dissolved 2.6 g (0.01 mole) of 7-(2,3-epoxypropoxy)-2-ethoxycarbonylbenzofuran obtained in Reference Example 9 in 15 ml of chloroform, and thereto 2 ml of concentrated hydrochloric acid was added. Thereafter, the mixture was vigorously stirred at room temperature for 15 minutes. After the chloroform layer was washed with water, the layer was dried with magnesium sulfate, and then the solvent was distilled away from the reaction mixture under reduced pressure. The resultant residue was purified by silica-gel column-chromatography (eluent:n-hexane:methylene chloride=1:1) to give the desired compound.

Workup

  1. washAfter the chloroform layer was washed with water
  2. dry with materialthe layer was dried with magnesium sulfate
  3. distillationthe solvent was distilled away from the reaction mixture under reduced pressure
  4. customThe resultant residue was purified by silica-gel column-chromatography (eluent:n-hexane:methylene chloride=1:1)

Sources & evidence

ORD record
ord-6d02b31ca98f480b987f2eebceb766d9
Source dataset
uspto-grants-1987_03
Patent number
US04652566

Reaction notes

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