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

HRID 410531

反応式

HRID 410531 の反応式
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

参加物

5

反応物 3

HCID 9256ThiazoleHCID 70721Dicyclopropyl ketoneHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0581596923da4abeb91e5e0af4170c6e
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

関連ノート

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