Potassium Carbonate → 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine

HRID 357506노트

반응식

HRID 357506 반응식
[CH2:1]([O:5][CH2:6][C:7]1[C:8]([O:14][CH3:15])=[N:9][CH:10]=[CH:11][C:12]=1I)[CH:2]=[CH:3][CH3:4].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:3]([C:2]1[C:12]2[C:7](=[C:8]([O:14][CH3:15])[N:9]=[CH:10][CH:11]=2)[CH2:6][O:5][CH:1]=1)[CH3:4]

참가 물질

7

반응물 2

HCID 11430Potassium CarbonateHCID 544155093-(But-2-enyloxymethyl)-4-iodo-2-methoxypyridine

생성물 1

HCID 106315694-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 178479813HCID 178479813, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-(but-2-enyloxymethyl)-4-iodo-2-methoxy-pyridine (228 g, 0.714 mol), potassium carbonate (200 g, 1.45 mol) and tetrabutylammonium chloride (100 g, 0.36 mol) in N,N-dimethylformamide (3.5 L) is purged with nitrogen for 20 min prior to the addition of palladium(II) acetate (3.75 g, 0.0167 mol) and tris(triphenylphosphine) rhodium(I) chloride (5.31 g, 0.00574 mol). The mixture is heated at 90° C. for about 4 h, cooled to below 50° C. and filtered through a pad of Celite®. The pad is washed with tert-butyl methyl ether (200 ml). The filtrate is washed with water (4×3 L), dried over sodium sulfate (260 g) and concentrated to a dark oil that is vacuum distilled (about 85°-98° C., about 6 mm Hg) to provide 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine as a yellow-orange oil which contains a 14.3:1 ratio of 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine to the corresponding double bond isomer, 4-ethylidene-8-methoxy-3,4-dihydro-1H-pyrano[3,4-c]pyridine.

후처리

  1. customis purged with nitrogen for 20 min
  2. temperaturecooled to below 50° C.
  3. filtrationfiltered through a pad of Celite®
  4. washThe pad is washed with tert-butyl methyl ether (200 ml)
  5. washThe filtrate is washed with water (4×3 L)
  6. dry with materialdried over sodium sulfate (260 g)
  7. concentrationconcentrated to a dark oil that
  8. distillationdistilled (about 85°-98° C., about 6 mm Hg)

출처 및 근거

ORD 기록
ord-d7633b52d1c5453e905c31dfe8d11945
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840898

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