Trifluoroacetic acid → [6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methanol

HRID 1258581Notes

Reaction equation

HRID 1258581 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N+:7]=1[O-].C(O)(C(F)(F)F)=[O:15]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[N:7]=[C:8]([CH2:12][OH:15])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671899662-(1,3-Dioxolan-2-yl)-6-methylpyridine 1-oxide

Product 1

HCID 19361733[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methanolYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(1,3-dioxolan-2-yl)-6-methylpyridine 1-oxide (2.3 g, 12.69 mmol, 1 eq.) in 200 ml dry DCM was added TFA (6.66 g, 31.73 mmol, 2.5 eq.) via syringe, The reaction was stirred 2 hrs and was evaporated on RFE. The residue was redissolved in 200 ml DCM and 200 ml of 2M aqueous K2CO3 solution was added. Vigorously stirring was allowed for 2 hrs. The aqueous layer was separated and extracted with fresh DCM (2×100 ml). The organics were combined, washed with water (50 ml), brine (50 ml), dried over MgSO4 and concentrated to give [6-(1,3-dioxolan-2-yl)pyridin-2-yl]methanol (2.25 g, 84% yield) as a yellow oil.

Workup

  1. customwas evaporated on RFE
  2. dissolutionThe residue was redissolved in 200 ml DCM
  3. addition200 ml of 2M aqueous K2CO3 solution was added
  4. stirringVigorously stirring
  5. waitwas allowed for 2 hrs
  6. customThe aqueous layer was separated
  7. extractionextracted with fresh DCM (2×100 ml)
  8. washwashed with water (50 ml), brine (50 ml)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-37020bcb42864c8bbc747694b97ff871
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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