Ethylene Glycol → HCID 25181650, 화합물

HRID 1896024노트

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HRID 1896024 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO.I[C:14]1[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[N:26]=1>C(O)CCC.CCOC(C)=O.[Cu]I>[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:35][CH2:36][N:37]([C:14]3[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:38][CH2:39]2)[N:26]=1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 425531323-Iodo-2-propoxypyridineHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

생성물 1

HCID 25181650HCID 25181650, 화합물수율 10%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 2631-Butanol용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Into a flamed flask flushed with nitrogen a mixture of CuI (19.4 mg. 0.1 mmol)), K3PO4 (425 mg, 2 mmol), ethylene glycol (112 μL), 3-iodo-2-propoxypyridine (263 mg, 1 mmol) in 1 mL of n-Butanol were added 255 mg of the compound of Example 3 dissolved in 1 mL of n-Butanol. The suspension was heated at 100° C. for 5 h. The reaction mixture was then cooled to r.t., diluted with EtOAc, washed with aq., NaHCO3 and water, dried over Na2SO4 and evaporated to dryness in vacuo. After the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 8:2. affording the title product (32 mg, 10%).

후처리

  1. customInto a flamed flask flushed with nitrogen
  2. temperatureThe reaction mixture was then cooled to r.t.
  3. washwashed with aq., NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customAfter the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with PE-EtOAc 8:2

출처 및 근거

ORD 기록
ord-9487ee5ee34645b489a8be11a9b2cc21
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518916B2

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