Dicyclohexylcarbodiimide → 3-Benzylpyrrolylmethyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate

HRID 903805Notes

Reaction equation

HRID 903805 reaction equation
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:20][CH:21]1[CH:23]([C:24](O)=[O:25])[C:22]1([CH3:28])[CH3:27])[CH2:16][CH2:17][CH2:18][CH3:19].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C=O)C>[CH2:15]([O:20][CH:21]1[CH:23]([C:24]([O:14][CH2:13][C:9]2[NH:10][CH:11]=[CH:12][C:8]=2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:25])[C:22]1([CH3:27])[CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 155857682,2-Dimethyl-3-(pentyloxy)cyclopropane-1-carboxylic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 233351193-Benzylpyrrolylmethyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-benzylpyrrolylmethyl alcohol (1.8 mmol), 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylic acid (2.0 mmol) and 4-dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of DMF is added N,N'-dicyclohexylcarbodiimide (2 mmol). The reaction mixture is stirred, under nitrogen, for about two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a rotary chromatograph eluting with ether/hexane to yield 3-benzylpyrrolylmethyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. filtrationfiltered
  2. extractionextracted with water
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  5. dry with materialdried over calcium sulfate and solvent
  6. customevaporated
  7. customThe crude product is chromatographed on a rotary chromatograph
  8. washeluting with ether/hexane

Sources & evidence

ORD record
ord-3d59b7274b854f069582212afefe5936
Source dataset
uspto-grants-1980_10
Patent number
US04229352

Reaction notes

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