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

HRID 1469201ノート

反応式

HRID 1469201 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3ba859f9ba104090af2929a15cbc8a55
出典データセット
uspto-grants-2015_04
特許番号
US09006187B2

反応ノート

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