Hydrochloric Acid → 4-PYRIDINEPENTANOL

HRID 892461Notes

Reaction equation

HRID 892461 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]1[CH:13]=[CH:12]C(C)=[CH:10][CH:9]=1.Cl.C(=O)(O)[O-:17].[Na+]>O1CCCC1>[N:8]1[CH:13]=[CH:12][C:1]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:17])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79634-MethylpyridineHCID 516892Sodium BicarbonateHCID 178506676HCID 178506676, compound

Product 1

HCID 6428094-PYRIDINEPENTANOL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl lithium (1.8 M cyclohexane diethyl ether, 27.6 mL, 0.0497 mol) is slowly added to a stirring solution of 4-picoline (4.6 g, 0.0497 mol) in 50 mL of tetrahydrofuran under nitrogen. The solution is stirred for 20 minutes at room temperature and then cooled to 0° C. 2-(4-Chlorobutoxy)-3,4,5,6-2H-tetrahydropyran (6.4 g, 0.0332 mol) is slowly added to the reaction mixture and the mixture is stirred for 30 minutes at 0° C. The reaction mixture is refluxed for 12 hours, cooled, and 100 mL of 10% hydrochloric acid solution is added. The reaction mixture is stirred for another 12 hours and then made basic with a saturated solution of sodium bicarbonate and extracted with chloroform. The organic phase is dried (sodium sulfate) and evaporated in vacuo. The resulting residue is chromatographed on silica gel (ethyl acetate) to give 1.25 g of 5-(4-pyridinyl)-1 pentanol as a brown oil.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture is stirred for 30 minutes at 0° C
  3. temperatureThe reaction mixture is refluxed for 12 hours
  4. temperaturecooled
  5. stirringThe reaction mixture is stirred for another 12 hours
  6. extractionextracted with chloroform
  7. dry with materialThe organic phase is dried (sodium sulfate)
  8. customevaporated in vacuo
  9. customThe resulting residue is chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-34218392250040d79e8e844aa6d3cc59
Source dataset
uspto-grants-1992_06
Patent number
US05118691

Reaction notes

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