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

HRID 541917Notes

Reaction equation

HRID 541917 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 111373-NitrophenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 109440762-(3-Nitrophenoxy)tetrahydro-2H-pyranYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of m-nitrophenol (1.8 g, 13 mmol) in dichloromethane (13 mL) was treated with dihydropyran (1.7 mL, 19 mmol) followed by pyridinium p-toluenesulfonate (0.32 g, 1.2 mmol) and stirred at 25° C. for 16 h. The reaction mixture was diluted with dichloromethane and washed with 1:1 brine/water (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude oil. This material was purified by flash column chromatography to give the desired product (2.5 g, 88%) as a clear oil.

Workup

  1. washwashed with 1:1 brine/water (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a crude oil
  6. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-9048cf0a16ff4203927263d530667779
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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