m-Chloroperbenzoic acid → 2-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide

HRID 892500ノート

反応式

HRID 892500 の反応式
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:27])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acid2 回HCID 198956113,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

生成物 1

HCID 538205312-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide収率 76.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

130 mg of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran were dissolved in 10 ml of dichloromethane at room temperature and 93 mg of m-chloroperbenzoic acid were added. After 2 hours thin-layer chromatography indicated that some starting material was still present, whereupon further m-chloroperbenzoic acid was added until the reaction was complete. The mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water, dried over sodium sulphate and evaporated to give 105 mg of 2-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide in the form of an oil. NMR (300 MHz, CDCl3): 8.36-8.30 (1H, m) 7.21-7.04 (4H, m), 6.89-6.76 (3H, m), 5.36-5.25 (1H, m), 2.46 (1H, dd, 14Hz, 6.5Hz), 1.75 (1H, broad t, 14Hz), 1.44 (3H, s), 1.40 (3H, s). MS (EI): 255 (M+ , 238 (M+ --OH).

後処理

  1. additionwas added until the reaction
  2. washThe mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated

出典と根拠

ORDレコード
ord-e2c637847d394f0eb6888e5d78fedca3
出典データセット
uspto-grants-1992_06
特許番号
US05118694

反応ノート

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