2-Bromopyridine → HCID 21187637, 화합물

HRID 1383766노트

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HRID 1383766 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 21187637HCID 21187637, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71685d845e684a98b068436b77e94b05
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255315B1

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