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Formaldehyde → Ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate

HRID 1509528
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HRID 1509528 반응식
[N:1]1[C:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C=O.[C:17]([O-])(=[O:19])C.[Na+].[OH-].[Na+]>C(O)(=O)C.ClCCl>[OH:19][CH2:17][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 818807Ethyl imidazo[1,2-a]pyridine-2-carboxylate

생성물 1

HCID 18466901Ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate수율 36.3%

시약·촉매·용매 2

HCID 176Acetic Acid
용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl imidazo[1,2-a]pyridine-2-carboxylate (5.0 g) in acetic acid (30 ml) were added 37% formaldehyde (14 ml) and sodium acetate (8.0 g) at room temperature, and the reaction mixture was heated under reflux for 15 hr. The reaction mixture was cooled to room temperature and dissolved in dichloromethane. The mixture was adjusted to pH 8 with 10% aqueous sodium hydroxide solution at 0° C. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with dichloromethane-methanol (15:1) was concentrated under reduced pressure to give the object product (2.1 g).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 15 hr
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washa fraction eluted with dichloromethane-methanol (15:1)
  8. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3e8467486f3943a7b36a78b44d61d239
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221836B2

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