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Water → 3-Benzylpyrrolylmethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 903799
Notes
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Reaction equation

HRID 903799 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:21]([C:28]1[CH:32]=[CH:31][NH:30][C:29]=1[CH2:33]O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:33][C:29]3[NH:30][CH:31]=[CH:32][C:28]=3[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 233351473-Benzylpyrrolylmethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Catalyst
HCID 241BenzeneSolvent

Procedure

A mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (0.95 g, 3.95 mmol), thionyl chloride (0.342 ml, 4.74 mmol) and DMF (several drops) in 50 ml benzene is stirred at RT for 2 days. The solvent and excess thionyl chloride are evaporated under reduced pressure. The resulting acid chloride is dissolved in 50 ml benzene, and 3-benzylpyrrolylmethyl alcohol (3.95 mmol) and 0.482 g 4-dimethtylaminopyridine (3.95 mmol) are added. The mixture is left at 25° for 18 hours and then heated under reflux for 2 hours. The mixture is then poured into water and extracted with ether. The organic phase is washed with dilute HCl, sat. NaHCO3, water and brine, dried and concentrated under vacuum. The crude product is purified by preparative TLC developing with 20% ethyl acetate/hexane to yield 3-benzylpyrrolylmethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate (A; R is hydrogen, X=X' is methyl, W is oxygen, R1 is 4-chlorophenyl).

Workup

  1. customThe solvent and excess thionyl chloride are evaporated under reduced pressure
  2. dissolutionThe resulting acid chloride is dissolved in 50 ml benzene
  3. waitThe mixture is left at 25° for 18 hours
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ether
  7. washThe organic phase is washed with dilute HCl, sat. NaHCO3, water and brine
  8. customdried
  9. concentrationconcentrated under vacuum
  10. customThe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-cca25ef4cd0d40f89edff0ba43c0a1de
Source dataset
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04229352

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes