Cyclohexanone, 3,3-dimethyl- → 3,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

HRID 1430325노트

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HRID 1430325 반응식
[Li]CCCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1>O1CCCC1.CCOCC>[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]([CH2:6][N:7]2[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]2)([OH:20])[CH2:15]1

참가 물질

6

반응물 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

생성물 1

HCID 866813303,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

To a cold (−78° C.) solution of nBuLi (12.48 mL) in tetrahydrofuran (40 mL) was added a solution of 1,5-dimethyl-1H-pyrazole (3.0 g) in tetrahydrofuran (3 mL) dropwise. After stirring for 1 hour, a solution of 3,3-dimethylcyclohexanone (3.94 g) in tetrahydrofuran (3 mL) was added dropwise, and the reaction was allowed to warm to 0° C. After stirring for 1 hour, the reaction mixture was diluted with ether (100 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with a gradient of 3% to 25% ethyl acetate in hexanes, gave the title compound.

후처리

  1. stirringAfter stirring for 1 hour
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography
  7. washeluting with a gradient of 3% to 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-290c5eba49e04f258aeff12d1ec61d41
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940737B2

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