Benzyl Bromide → 2-Phenyl-1-(thiazol-2-yl)ethanone

HRID 1019172ノート

反応式

HRID 1019172 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:9][Si](C)(C)C)[C:7]#N.C(Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH2:7][C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[O:9])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 7498Benzyl BromideHCID 183987011,3-Thiazol-2-yl[(trimethylsilyl)oxy]acetonitrile

生成物 1

HCID 109980962-Phenyl-1-(thiazol-2-yl)ethanone収率 41.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of the product from Step 1 (0.4 g, 1.9 mmol) in degassed THF (4 mL) at −78° C. was added LHMDs. After stirring at −78° C. for 15 min, benzyl bromide (0.27 mL, 2.3 mmol) was added, and stirring was continued at −78° C. for 15 min, followed by 1 h at r.t. The reaction was then quenched by the addition of saturated NH4Cl solution, and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc:hexane) to give 0.16 g of the product.

後処理

  1. stirringstirring
  2. waitwas continued at −78° C. for 15 min
  3. waitfollowed by 1 h at r.t
  4. customThe reaction was then quenched by the addition of saturated NH4Cl solution
  5. extractionthe product was extracted with EtOAc
  6. washThe organic layer was washed with H2O and brine
  7. dry with materialwas then dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (1:10 EtOAc:hexane)

出典と根拠

ORDレコード
ord-082dd7de13a045569fc80662d61fcfd0
出典データセット
uspto-grants-2002_11
特許番号
US06486142B2

反応ノート

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