Isopropanol → HCID 14476651, compound

HRID 1089910Notes

Reaction equation

HRID 1089910 reaction equation
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].Cl[C:8]1[C:13]([C:14]2[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=2)=[CH:12][CH:11]=[CH:10][N:9]=1>O1CCCC1>[CH3:19][C:17]1([CH3:20])[CH2:16][O:15][C:14]([C:13]2[C:8]([O:6][CH:3]([CH3:5])[CH3:4])=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:18]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 14476648HCID 14476648, compound

Product 1

HCID 14476651HCID 14476651, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12 g of sodium hydride (50% in oil=0.25 mole) are added during 10 minutes to 150 ml of dry tetrahydrofuran and 40 ml of isopropanol to give a suspension, the temperature of which rises to 50° C. A solution of 10.52 g (0.05 mole) of 2-chloro 3-(4,4-dimethyl 2-oxazolinyl)pyridine in 30 ml of dry tetrahydrofuran is then added during 20 minutes and the mixture is left to stand for 1.25 hours at ambient temperature. Excess isopropanol and the tetrahydrofuran are then removed under a partial vacuum and the residue is taken up in 50 ml of water and 100 ml of diisopropyl ether. The ethereal phase is then evaporated under reduced pressure to give 12.5 g of 3-(4,4-dimethyl 2-oxazolinyl)2-isopropoxy pyridine in the form of a clear brown oil.

Workup

  1. customto give a suspension
  2. customrises to 50° C
  3. waitthe mixture is left
  4. customExcess isopropanol and the tetrahydrofuran are then removed under a partial vacuum
  5. customThe ethereal phase is then evaporated under reduced pressure

Sources & evidence

ORD record
ord-b14f5ce6633e44ec8e523bd013a67b75
Source dataset
uspto-grants-1992_01
Patent number
US05079363

Reaction notes

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