1-methyl-1H-imidazole-5-carbaldehyde → (1-Methyl-1H-imidazol-5-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

HRID 731195

반응식

HRID 731195 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.[CH3:16][N:17]1[C:21]([CH:22]=[O:23])=[CH:20][N:19]=[CH:18]1>C1COCC1>[CH3:16][N:17]1[C:21]([CH:22]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)[OH:23])=[CH:20][N:19]=[CH:18]1

참가 물질

4

반응물 2

HCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 178419637HCID 178419637, 화합물

생성물 1

HCID 57835802(1-Methyl-1H-imidazol-5-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol수율 97.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (110 mL, 0.5 M in THF, 55 mmol) was added dropwise to a solution of 1-methyl-1H-imidazole-5-carbaldehyde (4.7 g, 50 mmol) in THF (790 mL) at −78° C. After stirring −78° C. for 2 hours, the reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), and the organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 14 g of the crude product 74.1, which was used in the next reaction without further purification.

후처리

  1. customthe reaction was quenched with saturated NH4Cl (aq)
  2. temperaturewarmed to room temperature
  3. extractionThe mixture was extracted with EtOAc (500 mL)
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0726f1e1e6cb44e1aed365d18742bd22
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582803B2

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