Hexane → HCID 19907485, compound

HRID 2371535Notes

Reaction equation

HRID 2371535 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.[CH3:30][CH2:31][CH2:32][CH2:33]CC>CC1C=CC=CC=1C>[O:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[O:23][CH2:22][CH2:21][CH2:20][CH2:1][C:2]1[CH:5]=[CH:18][CH:16]=[CH:15][C:3]=1[CH2:10][CH2:9][CH2:8][CH2:7][O:13][CH:12]1[CH2:33][CH2:32][CH2:31][CH2:30][O:14]1

Participants

7

Reactant 5

HCID 8058Hexane4×HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 18522661Acetone cardiceHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 19907485HCID 19907485, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 17.5 ml of absolute n-hexane were added 530 mg of o-xylene and 1.40 g of potassium tert.-butoxide, followed by dropwise addition of 8.4 ml of 1.6M 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 vermilion-colored suspension. The suspension was cooled with dry ice/acetone, and after adding at once solution of 4.46 g 2-(3-bromopropyloxy)tetrahydropyran in 2.5 ml of absolute n-hexane with stirring, further stirred for 5 minutes, warmed to a room temperature, and stirred overnight. To a yellow suspension thus obtained were added 20 ml of ice water and 50 ml of n-hexane. The organic layer was separated, washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure. The resulting oily residue was applied to a silica gel column, and eluted with hexane/ethyl acetate (20:1) to obtain 747 mg of crude 1,2-bis[4-(2-tetrahydropyranyloxy)butyl]benzene as a colorless liquid.

Workup

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

Sources & evidence

ORD record
ord-3ee387b3ea824639aa0f30332bf2e738
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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