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

HRID 2090937노트

반응식

HRID 2090937 반응식
[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

참가 물질

4

반응물 2

HCID 433815061-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde2회HCID 178419651HCID 178419651, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ed8a2177630a421997aac9cdeda2e5c1
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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