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

HRID 1858282Notes

Reaction equation

HRID 1858282 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>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 109006552-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyranYield 93%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.9 g (38.7 mmol) of 4-nitrobenzyl alcohol, 17.6 ml(193.5 mmol) of 3,4-dihydro-2H-pyran and 500 mg (2.6 mmol) of p-toluene sulfonic acid monohydrate in 200 ml of dichloromethane was stirred at room temperature for 4 hours. The reaction mixture was evaporated and the residue purified by flash chromatography on silica gel, using 1:4 ethyl acetate/hexane as eluent. Product containing fractions were combined and evaporated to give 8.52 g (93%) of 2-(4-nitrobenzyloxy)-tetrahydropyran as a pale yellow oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by flash chromatography on silica gel
  3. additionProduct containing fractions
  4. customevaporated

Sources & evidence

ORD record
ord-482af6a3cfdd412c8a9ac12d7808adc5
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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