Cyclooctanone → 1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

HRID 336613노트

반응식

HRID 336613 반응식
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[C:13]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCCC1>[CH3:12][C:11]1[N:7]([CH2:6][C:13]2([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 10403CyclooctanoneHCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

생성물 1

HCID 866812711-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a cold (−78° C.) solution of n-butyllithium (10 mL, 2.5M) in tetrahydrofuran (20 mL) was added 1,5-dimethyl-1H-pyrazole (2.0 g) in tetrahydrofuran (10 mL) dropwise via syringe. After 1 hour, cyclooctanone (2.63 g) in tetrahydrofuran (5 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous layer was extracted twice with additional ethyl acetate. The combined organics were dried over Na2SO4, filtered, and concentrated to provide the title compound.

후처리

  1. customThe mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with additional ethyl acetate
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2ee156e0504b4829b44c46e22f549efd
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889675B2

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