Methanol → Methyl 4-tetradecylpyrrole-2-carboxylate

HRID 1090738

반응식

HRID 1090738 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9b2e8f931aa4419a2c8bd392d24d895
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082856

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