Methanol → Methyl 4-tetradecylpyrrole-2-carboxylate

HRID 1090738

Reaction equation

HRID 1090738 reaction equation
B#B.[C:3]([C:18]1[CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[NH:21][CH:22]=1)(=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO.O>O1CCCC1>[CH2:3]([C:18]1[CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[NH:21][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6328200DiboronHCID 15023256Methyl 4-tetradecanoylpyrrole-2-carboxylate

Product 1

HCID 19371041Methyl 4-tetradecylpyrrole-2-carboxylateYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (30 ml, 90 mmol) of ca. 3M diborane in tetrahydrofuran was added to 1.80 g (5.4 mmol) of methyl 4-tetradecanoylpyrrole-2-carboxylate prepared in Synthetic Example 6, and then 1 ml of boron trifluoride-diethyl ether complex was further added thereto. The mixture was allowed to stand overnight at room temperature. Methanol and water were successively added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/3) to obtain 0.22 g (13% yield) of methyl 4-tetradecylpyrrole-2-carboxylate, m.p. 80°-82° C.

Workup

  1. customprepared in Synthetic Example 6
  2. addition1 ml of boron trifluoride-diethyl ether complex was further added
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue was purified

Sources & evidence

ORD record
ord-a9b2e8f931aa4419a2c8bd392d24d895
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Linked notes

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