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

HRID 2246652ノート

反応式

HRID 2246652 の反応式
[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

参加物

4

反応物 2

HCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 178419637HCID 178419637、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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 4.1, which was used in the next reaction without further purification.

後処理

  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

出典と根拠

ORDレコード
ord-b509942a6af4414fb949ed91d3309c4d
出典データセット
uspto-grants-2010_03
特許番号
US07687526B2

反応ノート

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