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

HRID 570295Notes

Reaction equation

HRID 570295 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-2024e2e9592e4800895b7c74f9590c15
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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