Hydrochloric Acid → (3-Methylthiophen-2-yl)(4-propylphenyl)methanone

HRID 1469201노트

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HRID 1469201 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](OCC)=[CH:4][CH:3]=1.[Li][CH2:12][CH2:13][CH2:14]C.CON(C)[C:19]([C:21]1[S:22][CH:23]=[CH:24][C:25]=1[CH3:26])=[O:20].Cl>C1COCC1>[CH3:26][C:25]1[CH:24]=[CH:23][S:22][C:21]=1[C:19]([C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH2:13][CH3:14])=[CH:6][CH:7]=1)=[O:20]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 685234-BromophenetoleHCID 10511733N-methoxy-N,3-dimethylthiophene-2-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 43462760(3-Methylthiophen-2-yl)(4-propylphenyl)methanone수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 4-bromophenetole (1.86 mL, 13.0 mmol) in anhydrous THF (15 mL) was added dropwise (over a 5-min period) a solution of n-BuLi (6.0 mL, 2.5 M in hexane) under nitrogen atmosphere at −78° C. The resulting mixture was stirred at −78° C. for 1 hour, and then a solution of the Weinreb amide 43 (1.85 g, 10.0 mmol) in anhydrous THF (5.0 mL) was added dropwise (over a 10-min period). The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into a 1 M HCl solution (25 mL) and extracted with EtOAc (50 mL). The organic phase was subsequently washed with brine, dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (4-ethoxyphenyl)(3-methylthiophen-2-yl)methanone (44, 1.52 g, 6.16 mmol, 62%).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic phase was subsequently washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customThe residue was further purified by silica column chromatography (Biotage)

출처 및 근거

ORD 기록
ord-3ba859f9ba104090af2929a15cbc8a55
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006187B2

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