Hydrochloric Acid → 1-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanone

HRID 30607ノート

反応式

HRID 30607 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[CH2:7][N:8]([CH3:10])[CH3:9].[CH2:14]([O:18]C=C)[CH2:15]CC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:9][N:8]([CH2:7][C:6]1[CH:11]=[C:2]([C:14](=[O:18])[CH3:15])[CH:3]=[CH:4][C:5]=1[O:12][CH3:13])[CH3:10]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 8818661-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine

生成物 1

HCID 8170251-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanone収率 42%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(5-Bromo-2-methoxy-benzyl)-dimethyl-amine (29 mmol), Butoxy-ethene (100 mmol), Palladium acetate (0.9 mmol), 1,3-Bis(diphenylphosphino)propane (1.8 mmol), and potassium carbonate were suspended in DMF (50 ml) and H2O under argon. Heated at 80° C. overnight. Poured into hydrochloric acid (2 M) and stirred for 1 hour. The mixture was adjusted to basic pH and extracted with CH2Cl2. The organic phase was evaporated on celite and the residue was purified by flash chromatography to give the title product as orange oil in 42% yield. 1H-NMR (CDCl3) δ 7.90 (s, 1H), 7.88 (dd, 1H), 6.89 (d, 1H), 3.88 (s, 3H), 3.44 (s, 2H), 2.55 (s, 3H), 2.25 (s, 6H).

後処理

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was evaporated on celite
  3. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-a917ce6dcd2d4fe08b04825b251cbac2
出典データセット
uspto-grants-2008_09
特許番号
US07423181B2

反応ノート

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