3,4-dihydro-2H-pyran → 2-[(2-Bromophenyl)methoxy]oxane

HRID 617402Notes

Reaction equation

HRID 617402 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 728502-Bromobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 53150262-[(2-Bromophenyl)methoxy]oxaneYield 99.3%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridinium p-toluenesulfonate (0.30 g) was added to a solution of 2-bromobenzylalcohol (25.00 g, 0.134 mol) in methylene chloride (100 ml), and the mixture was stirred at room temperature. 3,4-Dihydro-2H-pyran (16.86 g, 0.200 mol) was added thereto. The mixture was stirred at room temperature for 2 hours, and saturated aqueous sodium bicarbonate solution (200 ml) was added. The resulting mixture was extracted with methylene chloride and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave the desired compound 1-bromo-2-(tetrahydropyran-2-yloxy-methyl)benzene (36.00 g, 99.3%) as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-699808305f7049ddbe0bb5c901df6342
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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