Acetic Acid → HCID 20183659, compound

HRID 255590Notes

Reaction equation

HRID 255590 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C([Li])CCC.[CH2:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=[O:22])C>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:14]2([OH:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8078CyclohexaneHCID 142752-Methyl-5-hydroxypyridineHCID 178418339Butyllithium

Product 1

HCID 20183659HCID 20183659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-hydroxy-2-methylpyridine (10.66 g) in tetrahydrofuran (426 ml) was added a solution of n-butyllithium (1.5M in hexane, 143 ml) at -30°~-10° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour at room temperature. After cooling to -78° C., cyclohexane (11.14 ml) was added dropwise and allowed to warm to 0° C. and stirred for 30 minutes at 0° C. After addition of acetic acid (24.6 ml), the solvent was distilled off and the residue was diluted with ethyl acetate, and washed successively with water, 10% aqueous sodium hydrogen carbonate and aqueous saturated sodium chloride. After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated. The residue was washed with ethyl acetate to give 5-hydroxy-2-[(1-hydroxycyclohexyl)methyl]pyridine (11.96 g).

Workup

  1. temperatureAfter cooling to -78° C.
  2. temperatureto warm to 0° C.
  3. stirringstirred for 30 minutes at 0° C
  4. distillationthe solvent was distilled off
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed successively with water, 10% aqueous sodium hydrogen carbonate and aqueous saturated sodium chloride
  7. dry with materialAfter drying over magnesium sulfate
  8. extractionthe ethyl acetate extract
  9. filtrationwas filtered
  10. customevaporated
  11. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-ea76353bde2349ba9c6f8b8d8a47e8f5
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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