Allyl Alcohol → HCID 13336896, compound

HRID 128385Notes

Reaction equation

HRID 128385 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](Cl)=[C:5]([CH2:12][CH3:13])[N:4]=1)#[N:2].[CH2:14]([OH:17])[CH:15]=[CH2:16].[Na]>CC(C)=O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([O:17][CH2:14][CH:15]=[CH2:16])=[C:5]([CH2:12][CH3:13])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 5360545SodiumHCID 129071995-Chloro-6-ethylpyrazine-2,3-dicarbonitrile

Product 1

HCID 13336896HCID 13336896, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-5 °C

Procedure

2,3-Dicyano-5-chloro-6-ethylpyrazine (1.35 g; 0.007 mole) was dissolved in 30 ml of acetone, and while the solution was cooled to -5° C., a solution prepared from 20 ml of allylalcohol and 0.16 g (0.007 mole) of sodium was added dropwise. Then, the mixture was stirred for 30 minutes. The reaction mixture was poured into 200 ml of ice water, and the separated oily product was extracted with toluene. The toluene layer was concentrated under reduced pressure to afford a crude product. The resulting crude product was chromatographed on a column containing silica gel using toluene as an eluent to afford 1.00 g (yield 67%) of 2,3-dicyano-5-allyloxy-6-ethylpyrazine.

Workup

  1. additionwas added dropwise
  2. extractionthe separated oily product was extracted with toluene
  3. concentrationThe toluene layer was concentrated under reduced pressure
  4. customto afford a crude product
  5. customThe resulting crude product was chromatographed on a column
  6. additioncontaining silica gel

Sources & evidence

ORD record
ord-a57b85c6ab9043f391174b29f8633832
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

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