Phenol → 2-Phenoxypyrimidine

HRID 432180

반응식

HRID 432180 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 53247682-Phenoxypyrimidine

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4478a10157b48f79244caf147f3162b
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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