Methylparaben → methyl 4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzoate

HRID 507921ノート

反応式

HRID 507921 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH:14]=[O:15])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].O[C:40]1[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH2:14][O:15][C:40]2[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=2)=[CH:6][CH:7]=1

参加物

8

反応物 6

HCID 7456MethylparabenHCID 13831TributylphosphineHCID 62649Sodium sulfate decahydrateHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21226445Aluminium lithium hydrideHCID 231574845-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 23157684methyl 4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzoate収率 54.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (1.02 g, 5.0 mmol) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (200 mg, 5.27 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 hr. Sodium sulfate decahydrate (1.0 g) was added to the reaction mixture, and the mixture was allowed to warm to room temperature and stirred for 30 min. The insoluble material was filtered off, and the filtrate was concentrated to give a colorless oil. To this oil were added methyl 4-hydroxybenzoate (910 mg, 6.0 mmol), tributylphosphine (1.61 g, 8.0 mmol) and tetrahydrofuran (10 mL), and 1,1′-(azodicarbonyl)dipiperidine (1.50 g, 5.94 mmol) was added at room temperature. The mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane) to give the title compound (925 mg, yield 54%, 2 steps) as a yellow oil.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 30 min
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give a colorless oil
  6. additionwas added at room temperature
  7. stirringThe mixture was stirred at room temperature for 1 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-08d38202912f4cfbbd3e6f4a0c684b8f
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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