3-Benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamide → (3-Benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone

HRID 1445334ノート

反応式

HRID 1445334 の反応式
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17](N(OC)C)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:15])[CH3:16])[S:11][C:10]=1[C:17]([C:28]1[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 219612223-Benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamideHCID 178491912HCID 178491912、化合物

生成物 1

HCID 21961226(3-Benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
22 °C

実験手順

860 mg of 3-benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamide were dissolved in 50 ml of tetrahydrofuran (THF) and cooled to 0> C. in an ice bath, and 31.3 ml of 0.5 molar 4-methoxyphenymagnesium bromide solution in tetrahydrofuran were added. After 30 min, the ice bath was removed and the reaction mixture was warmed to 22° C. After one hour, 70 ml of saturated sodium bicarbonate solution were added to the reaction mixture, and it was extracted twice with 100 ml of methyl acetate each time. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:3).

後処理

  1. temperaturecooled to 0> C
  2. customthe ice bath was removed
  3. waitAfter one hour
  4. addition70 ml of saturated sodium bicarbonate solution were added to the reaction mixture, and it
  5. extractionwas extracted twice with 100 ml of methyl acetate each time
  6. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:3)

出典と根拠

ORDレコード
ord-2c7f5dfa33924f98a20a2d63849e888f
出典データセット
uspto-grants-2010_02
特許番号
US07666848B2

反応ノート

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