Phosphanium bromide → HCID 178438821、化合物

HRID 486028ノート

反応式

HRID 486028 の反応式
[CH2:1]([Li])CCC.[Br-].[PH4+].[C:8]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:15][C:14]2=[O:25])(=O)[CH3:9]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:21]([C:16]1[NH:17][C:18]2[C:13]([C:14](=[O:25])[N:15]=1)=[CH:12][C:11]([C:8]([CH3:1])=[CH2:9])=[CH:20][CH:19]=2)[CH2:22][CH2:23][CH3:24]

参加物

6

反応物 3

HCID 21868956Phosphanium bromideHCID 178418339ButyllithiumHCID 178441846HCID 178441846、化合物

生成物 1

HCID 178438821HCID 178438821、化合物

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a suspension of 3.66 g of methyltriphenylphosphonium bromide in 30 ml of dry tetrahydrofuran, cooled to -78° C., is added dropwise 5.9 ml of a 1.73M solution of n-butyllithium in hexanes. Following complete addition, the reaction mixture is allowed to warm to room temperature and stirred for 15 minutes, until all the phosphonium bromide is dissolved. The reaction mixture is then recooled to -78° C. and a suspension of 6-acetyl-2-butyl-4(1H)-quinazolinone in 15 ml of dry tetrahydrofuran is added. The reaction is allowed to warm to room temperature and stirred for 24 hours followed by quenching with saturated ammonium chloride solution. After diluting with 10 ml of water, the aqueous layer is extracted with chloroform and the combined organics dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 1:2 ethyl acetate-hexanes to give 0.23 g of the desired product as a white solid. CI MASS SPEC 243(MH+ ).

後処理

  1. additionaddition
  2. temperatureto warm to room temperature
  3. dissolutionis dissolved
  4. customis then recooled to -78° C.
  5. additionis added
  6. temperatureto warm to room temperature
  7. customby quenching with saturated ammonium chloride solution
  8. additionAfter diluting with 10 ml of water
  9. extractionthe aqueous layer is extracted with chloroform
  10. dry with materialthe combined organics dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue is purified by flash chromatography on silica gel
  14. washeluting with 1:2 ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-6ea1fd2a809f4503bc9f3286588e61d2
出典データセット
uspto-grants-1994_03
特許番号
US05290780

反応ノート

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