Trifluoroacetic acid → 4-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone

HRID 1748528노트

반응식

HRID 1748528 반응식
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1.[OH-].[Na+]>O>[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]2)=[N:13][CH:14]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 866924748-(5-Bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol

생성물 1

HCID 866924774-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone수율 41.7%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

Trifluoroacetic acid (11 ml) and water (1 ml) were added to 8-(5-bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (7.45 g) described in Reference Example 105(1) and stirred at room temperature. After completion of the reaction, water was added and neutralized by the addition of 1N aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxy-cyclohexanone (2.69 g) as a white solid.

후처리

  1. additionwas added
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5e63ee9959fd4148941415772d062957
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

반응 노트

불러오는 중…