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

HRID 1778935ノート

反応式

HRID 1778935 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ead138bcae7344b19599ffd9d4595adb
出典データセット
uspto-grants-2016_02
特許番号
US09266877B2

反応ノート

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