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Benzyl Alcohol → 2-(Benzyloxy)-6-chloropyrazine

HRID 1709701
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HRID 1709701 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.O>C1C=CC=CC=1>[CH2:1]([O:8][C:14]1[CH:15]=[N:16][CH:17]=[C:12]([Cl:11])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

생성물 1

HCID 117461652-(Benzyloxy)-6-chloropyrazine수율 86.5%

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

7.6 g of benzylalcohol was dissolved in 65 ml of benzene, and 2.8 g of 60% sodium hydride was added little by little to the solution under stirring not so as to foam too much at room temperature. After the addition, stirring was continued for 10 min. at room temperature, followed by reflux for 1 hour. Subsequently, the solution was cooled to 50° to 60° C., and added dropwise with a solution of 10 g of 2,6-dichloropyrazine in 65 ml of benzene for 10 min. Then, after reflux for 4 hours, the reaction was finished. After cooling below 10° C., about 100 ml of water was added, and the separated benzene layer was collected. The residue obtained by distilling off the solvent was purified by silica-gel column chromatography (developing solvent: n-hexane and ethyl acetate) to obtain 12.8 g of 2-benzyloxy-6-chloropyrazine as a colourless oil (yield: 86.5%) nD25 1.5818.

후처리

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureby reflux for 1 hour
  4. temperatureSubsequently, the solution was cooled to 50° to 60° C.
  5. temperatureThen, after reflux for 4 hours
  6. temperatureAfter cooling below 10° C.
  7. customthe separated benzene layer was collected
  8. customThe residue obtained
  9. distillationby distilling off the solvent
  10. customwas purified by silica-gel column chromatography (developing solvent: n-hexane and ethyl acetate)

출처 및 근거

ORD 기록
ord-28545ebfaa664ee0983592c789955f6d
출처 데이터셋
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04950679

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