2-Bromopyridine → HCID 21187637、化合物

HRID 1383766ノート

反応式

HRID 1383766 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[O:15][CH2:14]1.C(=O)(O)[O-:25].[Na+]>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1([OH:25])[CH2:20][CH2:21][C:16]2([O:23][CH2:13][CH2:14][O:15]2)[CH2:17][CH2:18]1

参加物

6

反応物 4

HCID 79732-BromopyridineHCID 516892Sodium BicarbonateHCID 123480741,4-Dioxaspiro[4.5]decan-6-oneHCID 178418339Butyllithium

生成物 1

HCID 21187637HCID 21187637、化合物

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

To a solution of 2-bromo-pyridine (10 g, 63.3 mmol) in tetrahydrofuran (200 mL) at −78° C. under an argon atmosphere was added a solution of n-butyllithium (26 mL of 2.5N solution, 65 mmol). The solution was stirred at −78° C. for 10 minutes and then a solution of cyclohexanedione monoethylene ketal (10 g, 64 mmol) in tetrahydrofuran(50 mL) was added. The reaction was allowed to warm to room temperature and poured into a saturated solution of sodium bicarbonate (mL) the mixture was extracted with ethyl acetate. The combined ethyl acetate fractions were dried over anhydrous sodium sulfate, filtered, and concentrated at reduced pressure. The residue was chromatographed over silica gel eluting with 25% to 50% ethyl acetate/hexane to give the product.

後処理

  1. temperatureto warm to room temperature
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate fractions were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed over silica gel eluting with 25% to 50% ethyl acetate/hexane
  7. customto give the product

出典と根拠

ORDレコード
ord-71685d845e684a98b068436b77e94b05
出典データセット
uspto-grants-2001_07
特許番号
US06255315B1

反応ノート

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