4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 15263943, compound

HRID 394956Notes

Reaction equation

HRID 394956 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH3:9].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl-].[Na+]>ClCCl>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:1][CH2:2][CH2:3][C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH3:9]

Participants

6

Reactant 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 15263943HCID 15263943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.09 ml of 5-(2-hydroxyethyl)-4-methylthiazole 93 is introduced into 150 ml of dichloromethane, 7.8 ml of 2,3-dihydropyran and 400 mg of pyridinium-p-toluenesulfonate are added, and it is stirred for 5 days at room temperature. Then, sodium chloride solution is added, extracted with ethyl acetate, the organic phase is washed with sodium bicarbonate solution and sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.8 g of 5-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]-4-methylthiazole 94 is obtained as a colorless oil.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with sodium bicarbonate solution and sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a06c12697d1d47ce9fed2f1f6a762f3d
Source dataset
uspto-grants-2003_08
Patent number
US06603031B1

Reaction notes

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