3,4-dihydro-2H-pyran → 2-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran

HRID 1277210Notes

Reaction equation

HRID 1277210 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 692754-Nitrobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 109006552-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyranYield 96.3%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitrobenzylalcohol (50 g, 0.326 mol) in ethyl acetate (EtOAc) (200 ml) were added 3,4-dihydropyran (35.7 ml, 0.392 mol) and CSA (camphor sulfonic acid) (379 mg, 1.63 mmol) under stirring at room temperature, and the mixture was stirred at room temperature for 1 hour. After the reaction completed, the reaction mixture was neutralized with saturated NaHCO3 solution and separated ethyl acetate layer was dried with MgSO4 and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 4-(2-tetrahydropyranyloxymethyl)nitrobenzene (74.5 g, 96%) as syrup.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customseparated ethyl acetate layer
  3. dry with materialwas dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-eba750070cc84e5097b144ca25a7ba3d
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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