Triethylsilane → methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

HRID 1894711ノート

反応式

HRID 1894711 の反応式
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[NH:9][CH:10]=1)=O.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:3]=1[CH2:4][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[NH:9][CH:10]=1

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 66646907methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 66646695methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
70 °C

実験手順

To a TFA 30 mL solution of methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate in a sealed tube was added triethylsilane (2.55 g, 22 mmol). The resulting reaction mixture was heated in an oil bath at 70° C. overnight. The reaction was concentrated and diluted with isopropylacetate and saturated sodium bicarbonate aqueous solution. The organic layer was separated. The aqueous layer was extracted with isopropylacetate twice. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes to give the title compound (840 mg).

後処理

  1. customThe resulting reaction mixture
  2. concentrationThe reaction was concentrated
  3. additiondiluted with isopropylacetate and saturated sodium bicarbonate aqueous solution
  4. customThe organic layer was separated
  5. extractionThe aqueous layer was extracted with isopropylacetate twice
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes

出典と根拠

ORDレコード
ord-d23573c4764441caa5d00332038117bf
出典データセット
uspto-grants-2013_08
特許番号
US08513289B2

反応ノート

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