Potassium tert-butoxide → 2-(4-Ethoxy-2,3-difluorophenyl)-5-vinylselenophene

HRID 1873397

反応式

HRID 1873397 の反応式
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[Se:20][C:19]([CH:21]=O)=[CH:18][CH:17]=2)=[C:12]([F:23])[C:11]=1[F:24])[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CC(OC)(C)C.O.Cl>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[Se:20][C:19]([CH:21]=[CH2:1])=[CH:18][CH:17]=2)=[C:12]([F:23])[C:11]=1[F:24])[CH3:8]

参加物

8

反応物 2

HCID 23665647Potassium tert-butoxideHCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

生成物 1

HCID 594563452-(4-Ethoxy-2,3-difluorophenyl)-5-vinylselenophene

試薬・触媒・溶媒 5

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

3.0 g (8.4 mmol) of methyltriphenylphosphonium bromide are initially introduced in 50 ml of THF at 0° C., and 0.89 g (7.9 mmol) of potassium tertbutoxide is dissolved in 7 ml of THF is added. After 1.5 h at RT, 2.0 g (6.4 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added, and the batch is stirred for 2.5 h. The mixture is diluted with MTBE, and water and 2 N hydrochloric acid are added. The organic phase is separated off, and the aqueous phase 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, n-heptane:EtOAc=10:1→5:1). Further purification is carried out by recrystallisation from n-heptane; 2-(4-ethoxy-2,3-difluorophenyl)-5-vinylselenophene is obtained as a yellow-orange solid.

後処理

  1. additionis added
  2. additionare added
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted with MTBE
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. customand dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=10:1→5:1)
  9. customFurther purification
  10. customis carried out by recrystallisation from n-heptane

出典と根拠

ORDレコード
ord-fe73d39bd56242818070e29deecf8535
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

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