Hydrochloric Acid → 2-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene

HRID 1873401ノート

反応式

HRID 1873401 の反応式
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[Se:43][C:42]([CH:44]=O)=[CH:41][CH:40]=2)=[C:35]([F:46])[C:34]=1[F:47])[CH3:31].Cl>C1COCC1.O>[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[Se:43][C:42]([CH:44]=[CH:2][CH2:3][CH3:4])=[CH:41][CH:40]=2)=[C:35]([F:46])[C:34]=1[F:47])[CH3:31]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 80374Propyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

生成物 1

HCID 722902482-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

14.1 g (35.0 mmol) of propyltriphenylphosphonium bromide are initially introduced in 150 ml of THF at 0° C., and 3.93 g (35.0 mmol) of potassium tert-butoxide dissolved in 50 ml of THF are added. After 1 h at this temperature, 9.0 g (28.6 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added as a solution in 300 ml of THF, and the batch is stirred at RT for 19 h. Water and 2 N hydrochloric acid are added to the mixture, and the batch is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). 2-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene is obtained as a reddish solid.

後処理

  1. additionare added
  2. extractionthe batch is extracted with MTBE
  3. washThe combined organic phases are washed with sat. sodium chloride soln
  4. customand dried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is purified by column chromatography (SiO2, toluene)

出典と根拠

ORDレコード
ord-abd2f197ce8b460f9cbfa4ef98e825ba
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

反応ノート

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