4-Methoxybenzyl alcohol → 2-Methoxy-5-(4-methoxybenzyloxy)pyridine

HRID 1948275노트

반응식

HRID 1948275 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][N:4]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[CH:5][N:4]=1

참가 물질

6

반응물 4

HCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 116223355-Hydroxy-2-methoxypyridine

생성물 1

HCID 693450322-Methoxy-5-(4-methoxybenzyloxy)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

According to Scheme 32 Method B: To a mixture of 2-methoxy-5-hydroxypyridine (2.87 mmol, 0.36 g), 4-methoxybenzyl alcohol (5.75 mmol, 0.72 mL) and PPh3 (5.29 mmol, 1.4 g) in THF (3.75 mL) cooled with an ice-water bath, was added dropwise DEAD (5.47 mmol, 0.86 ml). The resulting mixture was irradiated under microwave conditions at 90° C. for 30 minutes. The resulting reaction mixture was cooled, washed with a 1 N NaOH solution and extracted with AcOEt. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue triturated with diisopropyl ether. The precipitated obtained (PPh3O) was filtered off. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge heptane/CH2Cl2 80/20 yielding 2-methoxy-5-(4-methoxybenzyloxy)pyridine (339 mg, 48%).

후처리

  1. temperaturecooled with an ice-water bath
  2. customThe resulting mixture was irradiated under microwave conditions at 90° C. for 30 minutes
  3. customThe resulting reaction mixture
  4. temperaturewas cooled
  5. washwashed with a 1 N NaOH solution
  6. extractionextracted with AcOEt
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue triturated with diisopropyl ether
  11. customThe precipitated obtained (PPh3O)
  12. filtrationwas filtered off
  13. customThe residue was purified in a manifold (vac.)

출처 및 근거

ORD 기록
ord-e0cd7c5acac54025a00fe5400f8b3ee1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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