Trifluoroacetic anhydride → (3-Isopropylpyridin-2-YL)methanol

HRID 1987321Notes

Reaction equation

HRID 1987321 reaction equation
[CH:1]([C:4]1[C:5]([CH3:11])=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=[O:13]>C(Cl)Cl>[CH:1]([C:4]1[C:5]([CH2:11][OH:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydride2×HCID 235305783-Isopropyl-2-methyl-1-oxidopyridin-1-ium

Product 1

HCID 45091733(3-Isopropylpyridin-2-YL)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-isopropyl-2-methyl-pyridine 1-oxide (26.05 g, 173 mmol) in CH2Cl2 (690 mL) was added dropwise TFAA (51.83 mL) over 30 min. under N2 then stirred for an additional 3 h. Caution: exothermic reaction on addition of TFAA. The mixture was concentrated in vacuo to a minimum volume. Brine (200 mL) was added, basified to pH 9 with solid K2CO3 slowly, then the aqueous mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford (3-isopropyl-pyridin-2-yl)-methanol (26 g, 99%) as an orange oil. 1H NMR(CDCl3) δ 1.24 (d, 6H, 7.0 Hz), 2.92 (sep, 1H, J=6.6 Hz), 4.79 (s, 2H), 7.02-7.25 (m, 1H), 7.61 (d, 1H, J=7.9 Hz), 8.41 (d, 1H, J=4.8 Hz).

Workup

  1. customCaution: exothermic reaction
  2. concentrationThe mixture was concentrated in vacuo to a minimum volume
  3. additionBrine (200 mL) was added
  4. extractionthe aqueous mixture was extracted with CH2Cl2 (3×100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a344191f92a44249b84cffffe294adc
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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