Allyl bromide → ((2-(Allyloxy)pent-4-enyloxy)methyl)benzene

HRID 405778Notes

Reaction equation

HRID 405778 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([OH:16])[CH2:13][CH:14]=[CH2:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:17](Br)[CH:18]=[CH2:19]>C1COCC1>[CH2:19]([O:16][CH:12]([CH2:13][CH:14]=[CH2:15])[CH2:11][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 100354781-(Benzyloxy)pent-4-en-2-ol

Product 1

HCID 12996273((2-(Allyloxy)pent-4-enyloxy)methyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12).

Workup

  1. additionAfter addition
  2. temperaturewas cooled to 0° C
  3. temperaturethe resulting mixture was warmed to room temperature
  4. temperatureheated to 50° C. overnight
  5. temperatureAfter cooling to room temperature
  6. customthe mixture was quenched with saturated NH4Cl
  7. customThe residue was purified over silica

Sources & evidence

ORD record
ord-f9391ad3f9e24eab9ba4a508c82f6de1
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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