Water → 5-Benzyloxy-2-n-propylpyridine

HRID 1422075Notes

Reaction equation

HRID 1422075 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.C(=O)([O-])O.[Na+]>O1CCCC1.C(N(CC)CC)C.CS(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 42999103-Hydroxy-6-n-propylpyridine

Product 1

HCID 187069675-Benzyloxy-2-n-propylpyridineYield 452.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

5-Hydroxy-2-n-propylpyridine (13.72 g, 100 mmol) was dissolved in 200 ml of dry tetrahydrofuran under a nitrogen atmosphere, and at 0° C., 60% sodium hydride (7.0 g, 175 mmol) was added in small portions. The reaction mixture was stirred for 1/2 hour when a precipitate became visible. This precipitate was redissolved by adding 30 ml of dimethyl sulfoxide. Benzylbromide (13.1 ml, 18.84 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 3 hours. Water (200 mol) and 20 ml of triethylamine was added and The pH was adjusted to 12 with a saturated sodium hydrogen carbonate solution. The organic material was extracted into ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by destillation and gave 19.39 g (85%) of 5-benzyloxy-2-n-propylpyridine as an orange coloured oil. B.p. 160-170° C. 0.3 mbar. MS(SP): m/z 227 (m+). 1H-NMR (CDCl3, 200 MHz) δ: 0.95 (t, 3H); 1.72 (sext, 2H); 2.70 (t, 2H); 5.05 (s, 2H); 7.02 (d, 1H); 7.18 (dd, 1H); 7.24-7.46 (m, 5H); 8.30 (d, 1H).

Workup

  1. dissolutionThis precipitate was redissolved
  2. stirringthe resulting mixture was stirred at room temperature for 3 hours
  3. extractionThe organic material was extracted into ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe crude product was purified by destillation

Sources & evidence

ORD record
ord-d646de6a56854604b64e8c634409d6cd
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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