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

HRID 1073862노트

반응식

HRID 1073862 반응식
[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

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acid2회HCID 198956113,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-13a5e208ed194166929433de9436f904
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

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