Iodine → HCID 67399749, 화합물

HRID 70508

반응식

HRID 70508 반응식
II.Br[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1.[Mg].[CH:14]1([C:17]2[CH:18]=[CH:19][C:20]([CH:25]=[O:26])=[N:21][C:22]=2[O:23][CH3:24])[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([C:17]2[CH:18]=[CH:19][C:20]([CH:25]([C:4]3[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=3)[OH:26])=[N:21][C:22]=2[O:23][CH3:24])[CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 807IodineHCID 685234-BromophenetoleHCID 5462224MagnesiumHCID 86657999HCID 86657999, 화합물

생성물 1

HCID 67399749HCID 67399749, 화합물수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

A small amount of iodine was added to a suspension of 1-bromo-4-ethoxybenzene (484 μL) and magnesium (82.3 mg) in THF at room temperature in a nitrogen atmosphere, and the mixture was stirred at 50° C. for one hour. The reaction solution was returned to room temperature and a solution of 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde (300 mg) in tetrahydrofuran (1 mL) was added, followed by stirring at 50° C. for one hour. Tetrahydrofuran was concentrated under reduced pressure and a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was filtered through diatomaceous earth, and then the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→9:1) to give (5-cyclopropyl-6-methoxypyridin-2-yl)(4-ethoxyphenyl)methanol as a yellow oil (438 mg, 86%).

후처리

  1. customwas returned to room temperature
  2. stirringby stirring at 50° C. for one hour
  3. concentrationTetrahydrofuran was concentrated under reduced pressure
  4. additiona saturated ammonium chloride solution was added
  5. extractionfollowed by extraction with ethyl acetate
  6. filtrationThe organic layer was filtered through diatomaceous earth
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→9:1)

출처 및 근거

ORD 기록
ord-1d8f5338754f45f0bb6e0781d35a07a1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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