Phosphate → 2-(3-Bromopropoxy)tetrahydro-2H-pyran

HRID 2254189Notes

Reaction equation

HRID 2254189 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]1(C)C=[CH:10][C:9](S(O)(=O)=O)=[CH:8][CH:7]=1.P([O-])([O-])([O-])=[O:18]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][O:18]1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 6101p-Toluenesulfonic acidHCID 123083-Bromo-1-propanol

Product 1

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.61 g. 3-bromopropanol in 150 ml. methylene chloride at 0° C. was treated with 5.1 ml. dihydropropyran followed by 55 mg. p-toluenesulphonic acid and then warmed to room temperature. After one hour, phosphate buffer (pH: 7.5) was added to the mixture. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The yellow oil obtained was purified by chromatography on triethylamine-treated silica gel using a gradient solvent system (pure hexane-50% v/v ethyl ether/hexane) as eluent to give 2-(3-bromopropoxy)tetrahydro-2H-pyran in 69% yield as an oil, having a satisfactory NMR spectrum.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe yellow oil obtained
  5. customwas purified by chromatography on triethylamine-
  6. additiontreated silica gel using a gradient solvent system (pure hexane-50% v/v ethyl ether/hexane) as eluent

Sources & evidence

ORD record
ord-9bb79f4c4ff449a9b6deae3bc9c04018
Source dataset
uspto-grants-1993_08
Patent number
US05234942

Reaction notes

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