Tetrahydrofuran → HCID 15023382, compound

HRID 129338Notes

Reaction equation

HRID 129338 reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.[CH2:6]([C:19]1[NH:23][CH:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(O)CC>[CH2:6]([C:19]1[NH:23][CH:22]=[C:21]([C:24]([O:26][CH2:2][CH2:3][CH3:4])=[O:25])[CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 15023289HCID 15023289, compound

Product 1

HCID 15023382HCID 15023382, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
60 °C

Procedure

To 25 ml of tetrahydrofuran were added 1.50 g (5.11 mmol) of 5-tridecylpyrrole-3-carboxylic acid and 1.27 g (6.15 mmol) of dicyclohexylcarbodiimide, followed by adding 3.8 ml of n-propyl alcohol and 62 mg of dimethylaminopyridine. Then the mixture was heated at 60° C. for 10 hours under stirring. After cooling, the resulting precipitates were filtered off and washed well with ether. The filtrate and the washing liquid were combined and concentrated. The residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/20) to obtain 1.26 g (73% yield) of propyl 5-tridecylpyrrole-3-carboxylate, m.p. 51°-52° C.

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed well with ether
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-453226edff9a4a799c19e7680f0d34af
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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