3,4-dihydro-2H-pyran → 2-[(2-Chloro-4-methyl-5-nitrophenyl)methoxy]tetrahydro-2H-pyran

HRID 2173966ノート

反応式

HRID 2173966 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][OH:13].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86701534(2-Chloro-4-methyl-5-nitrophenyl)methanol

生成物 1

HCID 867015352-[(2-Chloro-4-methyl-5-nitrophenyl)methoxy]tetrahydro-2H-pyran

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2-chloro-4-methyl-5-nitrophenyl)methanol (23 g, 114 mmol) and 3,4-dihydro-2H-pyran (20.9 mL, 228 mmol) in CH2Cl2 (500 mL) was added pyridinium p-toluenesulfonate (5.7 g, 22.8 mmol), and then the mixture was stirred at room temperature for 11 h. The reaction was quenched by 5% aq. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by SiO2 column chromatography (heptane/EtOAc=96/4, isocratic) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 8.10 (s, 1H), 7.49 (s, 1H), 4.81 (d, J=13.64 Hz, 1H), 4.72-4.78 (m, 1H), 4.59 (d, J=13.64 Hz, 1H), 3.77-3.92 (m, 1H), 3.34-3.60 (m, 1H), 2.54 (s, 3H), 1.68-1.91 (m, 2H), 1.43-1.68 (m, 4H).

後処理

  1. customThe reaction was quenched by 5% aq. NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by SiO2 column chromatography (heptane/EtOAc=96/4, isocratic)

出典と根拠

ORDレコード
ord-86a7e58ae1ab4b3f9bc21e3154d8a303
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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