3,4-dihydro-2H-pyran → HCID 59838331, compound

HRID 708302Notes

Reaction equation

HRID 708302 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[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.C(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 59838331HCID 59838331, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6212ChloroformSolvent

Procedure

Pyridinium para-toluenesulfonate (0.01 g) was added to a chloroform solution containing 4-bromo-3,5-dimethylphenol (50 g) and 3,4-dihydro-2H-pyran (35 g), followed by stirring. After confirmation of the degree of reaction progress by thin-layer chromatography (hereinafter referred to as TLC), the reaction was quenched with triethylamine. The organic phase was washed with water and saturated brine in this order. The resulting organic phase was dried over anhydrous magnesium sulfate. Subsequently, the organic phase was concentrated and purified by column chromatography to obtain 70 g (yield: 980) of 2-(4-bromo-3,5-dimethylphenoxy)tetrahydropyran as a colorless liquid.

Workup

  1. customAfter confirmation of the degree of reaction progress by thin-layer chromatography (
  2. customwas quenched with triethylamine
  3. washThe organic phase was washed with water and saturated brine in this order
  4. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulfate
  5. concentrationSubsequently, the organic phase was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-52ecc4b162754369ae3a7211314deed3
Source dataset
uspto-grants-2015_11
Patent number
US09176257B2

Reaction notes

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