4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 15128981, compound

HRID 1006900Notes

Reaction equation

HRID 1006900 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][OH:9].[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][O:9][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 15128981HCID 15128981, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Methyl-5-thiazolyl)ethanol (25.71 g) was dissolved in tetrahydrofuran (200 ml), followed by the addition of 60% sodium hydride (7.185 g) under ice-cooling. The resulting mixture was stirred at room temperature for 1 hr. Thereafter, the it was ice-cooled again, followed by the addition of benzyl bromide (21.4 ml) and tetrabutylammonium bromide (665 mg). The resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (39.059 g, yield; 93%).

Workup

  1. temperaturecooling
  2. temperaturecooled again
  3. stirringThe resulting mixture was stirred at room temperature overnight
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-ad2129336d574035a3505b2bac84ddf4
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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