Phenol → 2-Phenoxypyrimidine

HRID 432180ノート

反応式

HRID 432180 の反応式
Cl[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.[OH-].[K+]>C1(C)C=CC=CC=1.O>[O:14]([C:5]1[N:4]=[CH:3][CH:2]=[CH:7][N:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

7

反応物 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 26541Dibenzo-18-crown-6HCID 126003845-Chloropyrimidine

生成物 1

HCID 53247682-Phenoxypyrimidine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A mixture of 5-chloropyrimidine (5.00 g, 0.0437 mol), phenol (5.38 g, 57.2 mmol), dibenzo-18-crown-6 (0.84 g, 0.0023 mol) and ground potassium hydroxide (5.92 g, 0.1055 mol) in toluene (75 ml) was heated at reflux for 3 hours with azeotropic removal of water. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The layers were separated and the aqueous phase was extracted with chloroform three times. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 2-phenoxypyrimidine as a white powder (95% pure, 4.56 g, 0.0265 mol): 1H NMR (CDCl3, 400 MHz) 8.57 (d, 2H), 7.43 (t, 2H), 7.26 (t, 1H), 7.20 (d 2H); TLC (n-heptane/ethyl acetate=1:1) Rf 0.42.

後処理

  1. temperaturewas heated
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between water and chloroform
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with chloroform three times
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-f4478a10157b48f79244caf147f3162b
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

反応ノート

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