Trifluoroacetic anhydride → [3-(1-Ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanol

HRID 250987Notes

Reaction equation

HRID 250987 reaction equation
[CH2:1]([C:3]([C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=[O:16].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH2:1]([C:3]([C:8]1[C:9]([CH2:14][OH:16])=[N:10][CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 672722723-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridine

Product 1

HCID 67272374[3-(1-Ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanolYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-ethyl-1-methoxy-propyl)-2-methyl-pyridine (0.185 g, 0.884 mmol) in CH2Cl2 (3 mL) was added TFAA (1 mL). The mixture was stirred for 24 h. K2CO3 (0.60 g, 4.3 mmol) in water (10 mL) was added. The aqueous mixture was extracted with CH2Cl2 (4×25 mL), and the combined organic layers were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (3:1 Et2O/CH2Cl2), affording [3-(1-ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanol as a yellow oil (0.111 g, 60%). 1H NMR (CDCl3) δ 0.70 (t, 6H, J=7.5 Hz), 1.76-1.88 (m, 2H), 1.89-2.01 (m, 2H), 3.06 (s, 3H), 4.93 (s, 2H), 7.21 (dd, 1H, J=7.8, 4.8 Hz), 7.56 (dd, 1H, J=7.8, 1.5 Hz), 8.47 (dd, 1H, J=4.8, 1.5 Hz).

Workup

  1. extractionThe aqueous mixture was extracted with CH2Cl2 (4×25 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationAfter filtration the solvent
  4. customwas removed by evaporation under vacuum
  5. customthe residue was purified by flash chromatography on a silica gel column (3:1 Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-3f202c254a164402b2507989fd32a822
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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