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

HRID 2173966Notes

Reaction equation

HRID 2173966 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-86a7e58ae1ab4b3f9bc21e3154d8a303
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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