Isopropanol → 1-(5-Hydroxy-2-neopentylpyridin-4-yl)ethanone

HRID 20016Notes

Reaction equation

HRID 20016 reaction equation
COC[O:4][C:5]1[C:6]([C:16](=[O:18])[CH3:17])=[CH:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:9][CH:10]=1.CC(O)C.C1COCC1>Cl>[OH:4][C:5]1[C:6]([C:16](=[O:18])[CH3:17])=[CH:7][C:8]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 575158761-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone

Product 1

HCID 575158771-(5-Hydroxy-2-neopentylpyridin-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone (21.6 g, 86 mmol) in (2:1:1) 5 M HCl: i-PrOH : THF (800 mL) was stirred 4 h at rt. The mixture was concentrated to remove the THF and i-PrOH. The resulting solution consisting of the product in aqueous HCl was quenched by slow addition to a solution of saturated aqueous NaHCO3 (500 mL) containing excess solid NaHCO3 (50 g). The aqueous layer was extracted with CH2Cl2 (3×250 mL), the organic layers combined and washed with saturated aqueous NaCl (250 mL), dried (MgSO4), and concentrated to give 1-(5-hydroxy-2-neopentylpyridin-4-yl)ethanone as a brown oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the THF and i-PrOH
  3. customwas quenched by slow addition to a solution of saturated aqueous NaHCO3 (500 mL)
  4. additioncontaining excess solid NaHCO3 (50 g)
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×250 mL)
  6. washwashed with saturated aqueous NaCl (250 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7537d8293d6048abad04b7051b233686
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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