Ethylenediaminetetraacetic Acid → 4-Methoxy-2-methylpyridine

HRID 273326

반응식

HRID 273326 반응식
[Cl-].C[Zn+].Cl[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1.[CH2:13](N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:13])[CH:10]=1

참가 물질

7

반응물 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 19911282-Chloro-4-methoxypyridineHCID 178477797HCID 178477797, 화합물

생성물 1

HCID 47377584-Methoxy-2-methylpyridine수율 50%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPh3)4 (0.161 g, 0.14 mmol) in THF (10 mL). The mixture was refluxed for 40 h and then poured into an aqueous solution (10 mL) containing ethylenediaminetetraacetic acid (1.5 g). The resulting mixture was neutralized with K2CO3 and extracted with Et2O. The organic layer was concentrated to give a residue, which was purified on a silica gel column eluting with MeOH:EtOAc (1:10) to give 4-methoxy-2-methylpyridine (0.213 g, 50.0%).

후처리

  1. temperatureThe mixture was refluxed for 40 h
  2. extractionextracted with Et2O
  3. concentrationThe organic layer was concentrated
  4. customto give a residue, which
  5. customwas purified on a silica gel column
  6. washeluting with MeOH:EtOAc (1:10)

출처 및 근거

ORD 기록
ord-e810fdf5a0ca4f1d9c55403b4f5a9099
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456289B2

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