N-Methyl-N-Methoxy-4-(3-indolyl)butyramide → Benzyl-3-(3-indolyl)propyl ketone

HRID 884

反応式

HRID 884 の反応式
CN(OC)[C:3](=[O:16])[CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([CH:6]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH2:5][CH2:4][C:3]([CH2:4][CH2:5][CH:6]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 11107631N-Methyl-N-Methoxy-4-(3-indolyl)butyramideHCID 178418336HCID 178418336、化合物

生成物 1

HCID 57064264Benzyl-3-(3-indolyl)propyl ketone収率 68.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 147 mg (0.60 mmol) of amide 139 in 4.0 mL of THF at -78° C. was added 1.31 mL (1.31 mmol) of benzylmagnesium chloride (1.0M in Et2O) and the reaction mixture was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with 5% KHSO4 and extracted into ether. The combined ethereal layers were washed with brine and dried over MgSO4. Flash chromatography (elution with 25% ether in hexane) gave 108 mg of the ketone 140. 1H NMR consistent with structure.

後処理

  1. customThe reaction was quenched with 5% KHSO4
  2. extractionextracted into ether
  3. washThe combined ethereal layers were washed with brine
  4. dry with materialdried over MgSO4
  5. washFlash chromatography (elution with 25% ether in hexane)

出典と根拠

ORDレコード
ord-70019092bb2c48d18020b5be4b31c9ad
出典データセット
uspto-grants-1998_03
特許番号
US05723459

関連ノート

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