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

HRID 1019172노트

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HRID 1019172 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-082dd7de13a045569fc80662d61fcfd0
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486142B2

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