Water → HCID 86631142, compound

HRID 912709Notes

Reaction equation

HRID 912709 reaction equation
C[O:2][CH:3](OC)[CH:4]([CH3:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.O.S(=O)(=O)(O)O>C1COCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][O:5][CH:4]([CH3:13])[CH:3]=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 67415336HCID 67415336, compound

Product 1

HCID 86631142HCID 86631142, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(2,2-dimethoxy-1-methylethoxy)methyl]pyridine (1.66 g, 7.85 mmol, obtained from Example 20(a)) in THF (30 mL) was added water (10 mL) and concentrated sulfuric acid (1 mL) and the resulting solution was refluxed for 12 h. After cooling to r.t., the volatile components were removed in vacuo and dichloromethane was added followed by saturated sodium bicarbonate solution until the aqueous layer was pH 7. The layers were separated and the aqueous phase was extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated yielding 0.875 g (68% yield) of the title compound. This material was used in the next step without further purification.

Workup

  1. temperaturethe resulting solution was refluxed for 12 h
  2. customthe volatile components were removed in vacuo and dichloromethane
  3. additionwas added
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-db2e2fa7f4cb4084808f26d0be1108ff
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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