Sodium hydride → methyl 4-formyl-1H-pyrrole-2-carboxylate

HRID 601791ノート

反応式

HRID 601791 の反応式
[H-].[Na+].[Br-].[C:4]([O:8]C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)(C)(C)C.C([C:33]1[NH:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1)=O>C1COCC1>[CH:4]([C:34]1[CH:35]=[C:36]([C:38]([O:40][CH3:41])=[O:39])[NH:37][CH:33]=1)=[O:8]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 316531methyl 5-formyl-1H-pyrrole-2-carboxylateHCID 2733853(tert-Butoxycarbonylmethyl)triphenylphosphonium Bromide

生成物 1

HCID 640310methyl 4-formyl-1H-pyrrole-2-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of NaH (5.74 g, 143.5 mmol; 60% in oil) in THF (200 mL) at 0° C. was added (tert-butoxycarbonylmethyl)triphenylphosphonium bromide (66 g, 143.5 mmol) as a solid in three portions. Cooling was removed and the mixture was stirred at rt for 30 min. It was then cooled to 0° C. and methyl 5-formyl-1H-pyrrole-2-carboxylate (16.9 g, 110.4 mmol) in THF (60 mL) was added dropwise over 40 min. The reaction mixture was allowed to warm to rt and was stirred overnight. Silica was added and the solvent was removed. The crude product was purified by flash chromatography (0-20% EtOAc/Heptane) to afford two isomeric compounds:

後処理

  1. temperatureCooling
  2. customwas removed
  3. temperatureIt was then cooled to 0° C.
  4. temperatureto warm to rt
  5. stirringwas stirred overnight
  6. additionSilica was added
  7. customthe solvent was removed
  8. customThe crude product was purified by flash chromatography (0-20% EtOAc/Heptane)
  9. customto afford two isomeric compounds

出典と根拠

ORDレコード
ord-d65970e3745d4b2fbb6552d84552b6e4
出典データセット
uspto-grants-2011_03
特許番号
US07902252B2

反応ノート

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