Epibromohydrin → HCID 22640963, compound

HRID 376938Notes

Reaction equation

HRID 376938 reaction equation
[H-].[Na+].[C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[OH:11])#[N:4].[CH2:12]([CH:14]1[O:16][CH2:15]1)Br>CN(C)C=O>[CH2:12]([O:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[C:3]#[N:4])[CH:14]1[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 27246492-Hydroxycyclohexane-1-carbonitrile

Product 1

HCID 22640963HCID 22640963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 60 mg, 1.59 mmol) was added to a solution of trans-2-cyanocyclohexanol in N,N-dimethylformamide (2.0 mL) and stirred for 10 minutes at room temperature. Epibromohydrin (0.22 g, 1.59 mmol) was then added and the reaction stirred for an additional 3 hours. The solution was partitioned between diethyl ether/water, and the layers separated. The ether layer was washed with water (3×100 mL) and dried over magnesium sulfate and evaporated to give 0.17 g of 2-cyanocyclohexyl glycidyl ether.

Workup

  1. stirringthe reaction stirred for an additional 3 hours
  2. customThe solution was partitioned between diethyl ether/water
  3. customthe layers separated
  4. washThe ether layer was washed with water (3×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9697a84621f446f39f3800e72bb7b41e
Source dataset
uspto-grants-2000_02
Patent number
US06022894

Reaction notes

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