(2-Methylbenzyl)triphenylphosphonium bromide → HCID 22678406、化合物

HRID 1837764

反応式

HRID 1837764 の反応式
[Br-].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:35][O:36][C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47]([CH:50]=O)[CH2:46][CH2:45]2)=[CH:41][CH:40]=[CH:39][N:38]=1>CN(C)C=O>[CH3:35][O:36][C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47](/[CH:50]=[CH:9]/[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH3:2])[CH2:46][CH2:45]2)=[CH:41][CH:40]=[CH:39][N:38]=1

参加物

5

反応物 3

HCID 197738(2-Methylbenzyl)triphenylphosphonium bromideHCID 22678407HCID 22678407、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 22678406HCID 22678406、化合物収率 68.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

In N,N-dimethylformamide (10 ml) was suspended 1.15 g of [(2-methylphenyl)methyl]triphenylphosphonium bromide. To the suspension was added 288 mg of potassium tert-butoxide, followed by stirring for 15 minutes under ice-cooling. A solution of 500 mg of 1-[(2-methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde dissolved in 3 ml of N,N-dimethylformamide was added dropwise thereinto, followed by stirring at room temperature overnight. Ice-water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to give 473 mg of the title compound as a pale yellow oil.

後処理

  1. temperaturecooling
  2. additionwas added dropwise
  3. stirringby stirring at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-5008ffafba3d4d41b0877944cafd41a9
出典データセット
uspto-grants-2004_08
特許番号
US06784192B2

関連ノート

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