Water → HCID 24763527, compound

HRID 1058847Notes

Reaction equation

HRID 1058847 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].[C:11]([O:15][C:16](=[O:19])[CH2:17]Br)([CH3:14])([CH3:13])[CH3:12].O>C1COCC1>[C:11]([O:15][C:16](=[O:19])[CH2:17][O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 24763527HCID 24763527, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 mL (5.18 mmol) 2-pyridylmethanol in 20 mL THF at 0° C. was added 270 mg (6.75 mmol) NaH and the reaction stirred for 0.25 h. Then 0.82 mL t-butylbromoacetate was added and the reaction warmed to rt and stirred for 12 days. The reaction was poured into 100 mL H2O, extracted with CH2Cl2 (2×100 mL), the combined organic layers washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give 1.16 g (61%) as a brown oil.

Workup

  1. stirringstirred for 12 days
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto give 1.16 g (61%) as a brown oil

Sources & evidence

ORD record
ord-8129c02c2bcd4b318e61c32f6ca85635
Source dataset
uspto-grants-2003_02
Patent number
US06518285B2

Reaction notes

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