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

HRID 1748528ノート

反応式

HRID 1748528 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5e63ee9959fd4148941415772d062957
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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