Thiazole → Dicyclopropyl(1,3-thiazol-2-yl)methanol

HRID 410531

반응식

HRID 410531 반응식
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH:11]1([C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH2:13][CH2:12]1>C1COCC1>[CH:11]1([C:14]([CH:16]2[CH2:18][CH2:17]2)([C:7]2[S:6][CH:10]=[CH:9][N:8]=2)[OH:15])[CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 9256ThiazoleHCID 70721Dicyclopropyl ketoneHCID 178418339Butyllithium

생성물 1

HCID 49962381Dicyclopropyl(1,3-thiazol-2-yl)methanol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

n-Butyllithium (2.5 M in hexanes, 0.953 mL, 2.38 mmol) was added to a stirred, cooled −78° C. mixture of thiazole (0.169 mL, 2.383 mmol) in THF (5.0 mL) and the mixture was stirred at −78° C. for 15 min. A solution of the dicyclopropylmethanone (250 mg, 2.27 mmol) in THF (3.0 mL) was added dropwise and the mixture was stirred 30 min at −78° C. and then the temperature was allowed to reach room temperature. The reaction was quenched by addition of water and the mixture was extracted with ethyl acetate (3×). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give dicyclopropyl(1,3-thiazol-2-yl)methanol (412 mg, 2.110 mmol, 93% yield). MS APCI: [M-OH]+ m/z 179.0.

후처리

  1. stirringthe mixture was stirred 30 min at −78° C.
  2. customto reach room temperature
  3. customThe reaction was quenched by addition of water
  4. extractionthe mixture was extracted with ethyl acetate (3×)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0581596923da4abeb91e5e0af4170c6e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

연결된 노트

불러오는 중…