Benzyl Bromide → HCID 14642611, compound

HRID 2108206Notes

Reaction equation

HRID 2108206 reaction equation
[H-].[Na+].[CH2:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C(Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O1CCC[CH2:19]1>>[CH2:3]([O:9][CH:15]([CH3:14])[CH2:16][CH2:11][CH:12]=[CH2:13])[C:4]1[CH:19]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 699635-Hexen-1-ol

Product 1

HCID 14642611HCID 14642611, compound

Procedure

To a stirred mixture of sodium hydride (2.6g, 110 mmoles) in tetrahydrofuran (185 ml) under a nitrogen atmosphere was added a solution of 5-hexene-1-ol (10g, 100 mmoles) in tetrahydrofuran (15 ml). After stirring at room temperature for 0.5 hour, the mixture was briefly heated to reflux and then cooled. Benzyl bromide (21.4 g, 125 mmoles) was added, and the mixture was stirred at reflux for one hour. Stirring was continued overnight at room temperature, after which the mixture was concentrated on a rotary evaporator. The mixture was poured into water, and the aqueous layer was extraced with three portions of ether. The combined organic estracts were dried over sodium sulfate, filtered, and the solvent evaporated. Chromatography of the residue on silica gel using a gradient of 0 to 10% ethyl acetate-hexane as eluant gave the title product (11.2 g) as an oil. The structure was confirmed by 1H NMR spectrometry.

Workup

  1. temperaturethe mixture was briefly heated
  2. temperatureto reflux
  3. temperaturecooled
  4. stirringthe mixture was stirred
  5. temperatureat reflux for one hour
  6. stirringStirring
  7. waitwas continued overnight at room temperature
  8. concentrationafter which the mixture was concentrated on a rotary evaporator
  9. additionThe mixture was poured into water
  10. dry with materialThe combined organic estracts were dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-fd43f93473b94b4ea87e8c3f1f751924
Source dataset
uspto-grants-1990_06
Patent number
US04937357

Reaction notes

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