1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde → cyclohexyl[1-(2-chlorophenyl)-3-methyl-1H-pyrazol-4-yl]methanol

HRID 2090937ノート

反応式

HRID 2090937 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([CH3:15])=[N:9]1.[CH:16]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCCC1>[CH:16]1([CH:13]([C:11]2[C:10]([CH3:15])=[N:9][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:12]=2)[OH:14])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

4

反応物 2

HCID 433815061-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde2 回HCID 178419651HCID 178419651、化合物

生成物 1

HCID 66776953cyclohexyl[1-(2-chlorophenyl)-3-methyl-1H-pyrazol-4-yl]methanol収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution (5 mL) of 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde (0.27 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise under ice-cooling cyclohexylmagnesium bromide (2.0 mL, 1M tetrahydrofuran solution). After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.29 g, 79%) as a pale-yellow oil.

後処理

  1. additionwas added dropwise under ice-
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

出典と根拠

ORDレコード
ord-ed8a2177630a421997aac9cdeda2e5c1
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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