Methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate → Methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoate

HRID 1488158ノート

反応式

HRID 1488158 の反応式
[C:1]([C:3]1[CH:4]=[N:5][N:6](COCC[Si](C)(C)C)[C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]

参加物

4

反応物 1

HCID 90030276Methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate2 回

生成物 1

HCID 90030040Methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoate収率 49%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 12052Triethylsilane溶媒

実験手順

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate (compound 256.3, 1.9 g, 5.11 mmol) in triethylsilane (4 mL) and trifluoroacetic acid (8 mL). The resulting solution was stirred for 4 h at room temperature, then concentrated under reduced pressure. The pH of the residue was carefully adjusted to 7-8 with aqueous sodium bicarbonate (sat.), then the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent to obtain the title compound as a white solid (600 mg, 49%).

後処理

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent

出典と根拠

ORDレコード
ord-0435af20fbde4cfea6b95d7b0debf43c
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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