3,4-dihydro-2H-pyran → 2-Bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzene

HRID 1766852Notes

Reaction equation

HRID 1766852 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][C:9]=1[CH2:16][OH:17].[C:18](=[O:21])([O-])O.[Na+]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)[CH:11]=[CH:10][C:9]=1[CH2:16][O:17][CH:5]1[CH2:4][CH2:3][CH2:2][CH2:18][O:21]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyran2×HCID 516892Sodium BicarbonateHCID 18676617(2-Bromo-4-hydroxymethylphenyl)methanol

Product 1

HCID 211104512-Bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzeneYield 88%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydro(2H)pyran (7.22 g, 84.9 mmol) was added dropwise to a solution of 2-bromo-1,4-benzenedimethanol (7.76 g, 35.8 mmol) obtained from Example 1-(1) and p-toluenesulfonic acid monohydrate (340.2 mg, 1.80 mmol) in dichloromethane (180 ml) with stirring at 0° C. The mixture was stirred for 1 hour, and then 3,4-dihydro(2H)pyran (0.8 g, 9.3 mmol) was further added thereto. After the mixture was stirred for 40 minutes, a saturated aqueous solution of sodium hydrogen carbonate (100 ml) was added thereto, then the resulting mixture was stirred for 5 minutes, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to chromatography on a silica gel (250 g) column (eluent; ethyl acetate:hexane=1:10) to give the title compound (12.07 g, 88% yield) as an oil.

Workup

  1. stirringAfter the mixture was stirred for 40 minutes
  2. stirringthe resulting mixture was stirred for 5 minutes
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d01c17181e9a47dd9b67a9f020f08464
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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