2-Bromopyridine → HCID 21187637, compound

HRID 1383766Notes

Reaction equation

HRID 1383766 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 21187637HCID 21187637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-71685d845e684a98b068436b77e94b05
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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