Epibromohydrin → HCID 19391251, compound

HRID 1756809Notes

Reaction equation

HRID 1756809 reaction equation
[C:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:11]([CH:13]1[O:15][CH2:14]1)Br>CN(C=O)C.O>[O:15]1[CH2:14][CH:13]1[CH2:11][O:8][CH2:7][C:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 11251975HCID 11251975, compound

Product 1

HCID 19391251HCID 19391251, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

(Compound No. 229) 1,3-Cyclohexadiene-1-methanol (2 g, 0.0182 mol) synthesized in Example 21 was dissolved in DMF (10 ml) and 60% sodium hydride (775 mg, 0.0194 mol) was added at 0° C. The mixture was stirred for 10 minutes and a solution of epibromohydrin (3 g, 0.022 mol) in DMF (3 ml) was added dropwise. The mixture was stirred at room temperature for 1 hour and at 40° C. for 1 hour and the reaction mixture was poured in water, extracted with ethyl acetate and the combined ethyl acetate layer was washed with water, dried over sodium sulfate and the solvent was distilled off. The residue was separated and purified by silica gel column chromatography (silica gel 60 g, ethyl acetate:hexane=1:10) to obtain 1-(2,3-epoxypropoxymethyl)-cyclohexa-1,3-diene (2.31 g, 76%). This compound has the following NMR spectrum.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour and at 40° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washthe combined ethyl acetate layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (silica gel 60 g, ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-8f616a54b1bf4f27848dafcbfa475ae2
Source dataset
uspto-grants-1995_08
Patent number
US05442062

Reaction notes

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