3,4-dihydro-2H-pyran → 2-[(7-Bromoheptyl)oxy]tetrahydro-2H-pyran

HRID 1470678Notes

Reaction equation

HRID 1470678 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>C(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 662841-Heptanol, 7-bromo-

Product 1

HCID 5590082-[(7-Bromoheptyl)oxy]tetrahydro-2H-pyranYield 114.3%

Reagents, catalysts & solvents 2

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

Procedure

Dihydropyran (1 mL, 11.0 mmol) and pyridinium p-toluenesulfonate (148 mg, 0.59 mmol) were added to a solution of 7-Bromo-1-heptanol (1.1 g, 5.64 mmol) in CH2Cl2 (22 mL). After stirring overnight, the solution was washed with 1 M HCl (20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL). The solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (0%→50% ethyl acetate/hexanes) to give the title compound (1.8 g, >100%).

Workup

  1. washthe solution was washed with 1 M HCl (20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL)
  2. dry with materialThe solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (0%→50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a8dc77c5493b4c30a6ec6f23b19fe366
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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