Isopropanol → 1-(3-Hydroxy-6-neopentylpyridin-2-yl)ethanone

HRID 1697202Notes

Reaction equation

HRID 1697202 reaction equation
COC[O:4][C:5]1[C:6]([C:16](=[O:18])[CH3:17])=[N:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][CH:10]=1.CC(O)C.C1COCC1>Cl>[OH:4][C:5]1[C:6]([C:16](=[O:18])[CH3:17])=[N:7][C:8]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 575158431-(3-(Methoxymethoxy)-6-neopentylpyridin-2-yl)ethanone

Product 1

HCID 575158441-(3-Hydroxy-6-neopentylpyridin-2-yl)ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-(3-(methoxymethoxy)-6-neopentylpyridin-2-yl)ethanone (3.75 g, 15 mmol) in (2:1:1) 5 M HCl: i-PrOH:THF (100 mL) was stirred 16 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 (28 g). The aqueous layer was extracted with CH2Cl2 (3×100 mL), the organic layers combined and washed with saturated aqueous NaCl (100 mL), dried (MgSO4), and concentrated to give the crude product as a brown oil. The product was purified by ISCO (0-10% EtOAc/Hexanes) to give 1-(3-hydroxy-6-neopentylpyridin-2-yl)ethanone (1.98 g, 64% yield) as a clear, colorless 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 (28 g)
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  6. washwashed with saturated aqueous NaCl (100 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give the crude product as a brown oil
  10. customThe product was purified by ISCO (0-10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-9c58c76c457249f0996915003a45145f
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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