Ethyl Acetate → HCID 68407746、化合物

HRID 879159ノート

反応式

HRID 879159 の反応式
[CH3:1][CH:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:5]C=C1.C1C(=O)N([Br:24])C(=O)C1.C([O:28][CH2:29][CH3:30])(=O)C>C1COCC1.O>[Br:24][CH:30]1[CH:29]([OH:28])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:7][CH:2]1[CH3:1]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 59226560HCID 59226560、化合物

生成物 1

HCID 68407746HCID 68407746、化合物収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in THF and water (1:1, 0.13 M) was added NBS (1.5 equiv.) and the reaction was stirred at room temperature for 30 min. Upon completion, ethyl acetate and water were added to the reaction, the organic phase was dried with brine, then sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol as a yellow oil in 80% yield. LC/MS=315.0/313.0 (M+H), LC=2.966 min.

後処理

  1. dry with materialthe organic phase was dried with brine
  2. filtrationsodium sulfate, filtered
  3. concentrationconcentrated
  4. customThe crude material was purified via silica gel column chromatography
  5. washeluting with ethyl acetate and hexanes (1:1)

出典と根拠

ORDレコード
ord-7cbdf3ec107e4c1198ce5e72cfb6129a
出典データセット
uspto-grants-2015_03
特許番号
US08987457B2

反応ノート

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