2-Methoxypropene → HCID 67079339, compound

HRID 1047404Notes

Reaction equation

HRID 1047404 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].C[O:12][C:13]([CH3:15])=[CH2:14].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[CH:4]([O:12][CH:13]([CH3:15])[CH3:14])[O:5][CH3:16]

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 17836195(2,4-Dibromophenyl)methanolHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 67079339HCID 67079339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, to a solution of 2,4-dibromobenzyl alcohol (40 g, 0.15 mol) in tetrahydrofuran (300 ml) was added 2-methoxypropene (144 ml, 1.5 mol) at room temperature, and then the mixture was cooled to 0° C. At the same temperature, pyridinium p-toluenesulfonic acid (75 mg, 0.30 mmol) was added and the mixture was stirred for 1 hour. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate cooled to 0° C., and extracted with toluene. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the titled compound as an oil in quantitative yield. The product was used in the next step without further purification.

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with toluene
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-945da6a0736a4b13951141d77e5718fb
Source dataset
uspto-grants-2013_10
Patent number
US08569520B2

Reaction notes

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