Benzyl Alcohol → 4-(Benzyloxy)-6-chloropyrimidine

HRID 1592235ノート

反応式

HRID 1592235 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:15]=[CH:14][N:13]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

生成物 1

HCID 225998714-(Benzyloxy)-6-chloropyrimidine収率 96.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In 3 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% in oil), to which 0.5 ml of a tetrahydrofuran solution containing 0.22 g of benzyl alcohol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes and then cooled to 0° C., to which 0.5 ml of a tetrahydrofuran solution containing 0.3 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by stirring at 0° C. for 1.5 hours and then further stirring at room temperature for 4.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.43 g of 4-chloro-6-benzyloxypyrimidine.

後処理

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringby stirring at 0° C. for 1.5 hours
  5. stirringfurther stirring at room temperature for 4.5 hours
  6. extractionextracted three times with chloroform
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-711f6786fa1947fdba468695065c8adf
出典データセット
uspto-grants-2007_11
特許番号
US07291730B2

反応ノート

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