Hydrochloric Acid → (4-Benzyloxy-3-methoxy-phenyl)-(2-trifluoromethyl-pyridin-3-yl)-methanone

HRID 61989ノート

反応式

HRID 61989 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:26](=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[C:33]([F:36])([F:35])[F:34].Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:26]([C:27]2[C:28]([C:33]([F:36])([F:34])[F:35])=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:37])=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 71445792N-Methoxy-N-methyl-2-(trifluoromethyl)nicotinamideHCID 178418339Butyllithium

生成物 1

HCID 67037150(4-Benzyloxy-3-methoxy-phenyl)-(2-trifluoromethyl-pyridin-3-yl)-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-benzyloxy-3-methoxy-bromobenzene (2.0 g, 6.82 mmol) in tetrahydrofuran (50 mL) at −78° C. under argon was added 2 N butyllithium solution in hexanes (3.75 mL, 7.5 mmol) dropwise. The resulting mixture was allowed to stir for one hour, whereupon a solution of N-methoxy-N-methyl-2-trifluoromethyl-nicotinamide (1.76 g, 7.5 mmol) in tetrahydrofuran (20 mL) was added dropwise. The mixture was then allowed to reach room temperature over two hours, then poured onto cold 2 N aqueous hydrochloric acid (150 mL). The mixture was extracted with diethylether, and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent left a brown oil that was chromatographed over silica gel (petroleum ether/ethyl acetate, 2:1) to give (4-benzyloxy-3-methoxy-phenyl)-(2-trifluoromethyl-pyridin-3-yl)-methanone, 1.72 g (65%).

後処理

  1. additionwas added dropwise
  2. extractionThe mixture was extracted with diethylether
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customEvaporation of the solvent
  7. waitleft a brown oil that
  8. customwas chromatographed over silica gel (petroleum ether/ethyl acetate, 2:1)

出典と根拠

ORDレコード
ord-a5b2bc72e8ac4342abc43db5293baa10
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

反応ノート

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