Water → HCID 12857362, compound

HRID 1648864Notes

Reaction equation

HRID 1648864 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH:15]([CH2:18][CH:19]=[CH2:20])[CH2:16][OH:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C(Cl)(Cl)Cl>[Br:1][CH2:20][CH:19]1[CH2:18][CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:16][O:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57839416014-71-4

Product 1

HCID 12857362HCID 12857362, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.78 g) is added to a stirred solution of 1.6 g of 2-phenyl-4-penten-1-ol in 15 ml of chloroform at room temperature. The resulting mixture is stirred at room temperature for 3 hours. The reaction mixture is then poured into 10 ml of water. The chloroform layer is separated and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluant to give 1.67 g of 2-(bromomethyl)-4-phenyltetrahydrofuran as colorless oil.

Workup

  1. customThe chloroform layer is separated
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel with chloroform eluant

Sources & evidence

ORD record
ord-df2811c636024ec199a0bc5de9945e74
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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