Methanol → Methyl 4-tetradecylpyrrole-2-carboxylate

HRID 1090738

反応式

HRID 1090738 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 19371041Methyl 4-tetradecylpyrrole-2-carboxylate収率 13%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9b2e8f931aa4419a2c8bd392d24d895
出典データセット
uspto-grants-1992_01
特許番号
US05082856

関連ノート

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