4-Methylmorpholine → (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

HRID 2053752ノート

反応式

HRID 2053752 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=N1.CN1CCOCC1.N1CC=CC1>CN(C)C=O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[CH3:11])=[O:8])[CH2:20][CH:25]=[CH:24][CH2:23]1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 660593-PyrrolineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).

後処理

  1. additionThen it is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-13068a93f2ec4ec2ac10d0c3f94f8be7
出典データセット
uspto-grants-2008_02
特許番号
US07326791B2

反応ノート

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