Water → 1-(3-Furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 975050

Reaction equation

HRID 975050 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.[C:12]([C:15]1[S:19][CH:18]=[N:17][C:16]=1[CH3:20])(=[O:14])[CH3:13].O>C(OCC)C>[O:4]1[CH:5]=[CH:6][C:2]([C:12]([C:15]2[S:19][CH:18]=[N:17][C:16]=2[CH3:20])([OH:14])[CH3:13])=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 891643-BromofuranHCID 1622925-Acetyl-4-methylthiazoleHCID 178418339Butyllithium

Product 1

HCID 189363091-(3-Furyl)-1-(4-methyl-5-thiazolyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

3-Bromofuran (6.8 g) in diethylether (15 ml) was added dropwise to n-butyllithium (2.5M solution in hexane, 18.4 ml) in diethylether (20 ml) at -70° C. under a nitrogen atmosphere. After 1 hour, 5-acetyl-4-methylthiazole (5 g) in diethylether (15 ml) was added dropwise. After a further 3 hours at -70° C., the mixture was allowed to warm to room temperature and was then left overnight. The mixture was poured into water and extracted with diethylether. The product thus obtained was crystallised from diethylether, m.p. 102°-104° C.

Workup

  1. waitAfter a further 3 hours at -70° C.
  2. waitwas then left overnight
  3. extractionextracted with diethylether
  4. customThe product thus obtained
  5. customwas crystallised from diethylether, m.p. 102°-104° C.

Sources & evidence

ORD record
ord-bdf4f3d7eef34a679bd9eae33bcbd244
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Linked notes

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