Nitrogen → 1-[4-(Hydroxymethyl)pyridin-2-yl]ethan-1-one

HRID 2064993Notes

Reaction equation

HRID 2064993 reaction equation
N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16](=[O:18])[CH3:17])[CH:11]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16](=[O:18])[CH3:17])[CH:11]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 131729997HCID 131729997, compound

Product 1

HCID 206212741-[4-(Hydroxymethyl)pyridin-2-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanone (340 mg, 1.28 mmol) in dry THF (5 mL) was treated at 0° C. with TBAF (1.9 mL of a 1M solution in THF, 1.90 mmol). The reaction mixture was stirred at 0° C. for 5 min and at rt for 1 h30. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (5:1 to 1:3 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:2 hept-EA)=0.10. LC-MS-conditions 02: tR=0.40 min; [M+H]+=152.24.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by FC (5:1 to 1:3 hept-EA)

Sources & evidence

ORD record
ord-7a841980ad8041ca864eeca87e0daec6
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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