2-(3-Bromopropoxy)tetrahydro-2H-pyran → HCID 19907429, compound

HRID 2371533Notes

Reaction equation

HRID 2371533 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[C:12](=[O:14])=[O:13].[CH3:15][C:16]([CH3:18])=O.Br[CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1>CCCCCC.C1(C)C=CC=C(C)C=1>[O:13]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:12]1[O:14][CH2:15][CH2:16][CH2:18][CH2:1][C:2]1[CH:5]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:20][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:3]=1

Participants

7

Reactant 4

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 18522661Acetone cardiceHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 19907429HCID 19907429, compound

Reagents, catalysts & solvents 2

HCID 7929M-XyleneSolventHCID 8058HexaneSolvent4×

Procedure

To 17.5 ml of absolute n-hexane were added dropwise 530 mg of m-xylene and 1.40 g of potassium t-butoxide, followed by addition of 8.4 ml of 1.6M solution of n-butyl lithium in n-hexane over 5 minutes with stirring at a room temperature, and the mixture was refluxed for an hour to obtain a orange suspension. This reaction mixture was cooled with dry ice/acetone, and after adding at once a solution of 3.35 g 2-(3-bromopropyloxy)tetrahydropyran in absolute n-hexane with stirring, further stirred for 5 minutes, warmed to a room temperature and stirred at the same temperature overnight. To a pale yellow suspension thus obtained were added 20 ml of ice water and 50 ml of n-hexane. The separated organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to remove the solvent. The resulting oily residue was applied to a silica gel column and eluted with hexane/ethyl acetate (20:1) to obtain 913 mg of the title compound as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. customto obtain a orange suspension
  3. stirringwith stirring
  4. stirringfurther stirred for 5 minutes
  5. temperaturewarmed to a room temperature
  6. stirringstirred at the same temperature overnight
  7. customTo a pale yellow suspension thus obtained
  8. washThe separated organic layer was washed with water
  9. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  10. customevaporated under a reduced pressure
  11. customto remove the solvent
  12. washeluted with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-7cfd3683f0f24b1389bbbd542ce74602
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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