p-Toluenesulfonic acid → 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

HRID 658269Notes

Reaction equation

HRID 658269 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 779706-Bromo-1-hexanol

Product 1

HCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo hexan-ol (F) (2 g, 11 mmol) in CH2Cl2 (50 ml) was added dropwise dihyrdopyran (1.6 ml, 16.5 mmol) followed by para-toluenesulphonic acid (commercially available) (0.075 g). The reaction mixture was stirred at room temperature for 16 h. The dark blue solution was then washed with water (2×25 ml) then saturated hydrogen carbonate solution (25 ml) and finally with a saturated sodium chloride solution (25 ml). The organic phase was then dried (MgSO4) and the solvent was evaporated under reduced pressure. The crude material was then purified through flash silica gel chromatography (hexane/EtOAc, 10:1) to afford compound 2-(6-Bromo-hexyloxy)-tetrahydropyran (G) as an oil (0.5 g, 70%).

Workup

  1. washThe dark blue solution was then washed with water (2×25 ml)
  2. dry with materialThe organic phase was then dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude material was then purified through flash silica gel chromatography (hexane/EtOAc, 10:1)

Sources & evidence

ORD record
ord-15096605bc934cd5a8befa38fb27d1d7
Source dataset
uspto-grants-2011_12
Patent number
US08076426B2

Reaction notes

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