Water → 1-(4-Methyl-5-oxazolyl)-1-(3-thienyl)ethanol

HRID 2806

Reaction equation

HRID 2806 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.C([Li])CCC.[C:12]([C:15]1[O:19][CH:18]=[N:17][C:16]=1[CH3:20])(=[O:14])[CH3:13].O>C(OCC)C>[CH3:20][C:16]1[N:17]=[CH:18][O:19][C:15]=1[C:12]([C:2]1[CH:6]=[CH:5][S:4][CH:3]=1)([OH:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 133833-BromothiopheneHCID 110298391-(4-Methyloxazol-5-yl)ethanoneHCID 178418339Butyllithium

Product 1

HCID 189363241-(4-Methyl-5-oxazolyl)-1-(3-thienyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

3-Bromothiophene (4.23 g) in diethylether (10 ml) was added dropwise to n-butyllithium (2.5M solution in hexane, 10.4 ml) in dry diethylether (20 ml) at -70° C. under a nitrogen atmosphere. After 3 hours 5-acetyl-4-methyloxazole (2.5 g) in diethylether (10 ml) was added dropwise. After a further 2.5 hours at -70° C., the mixture was allowed to warm to room temperature and then left overnight. The mixture was poured into water and extracted with ether. The product thus obtained was crystallised from diethylether to give 1-(4-methyl-5-oxazolyl)-1-(3-thienyl)ethanol, m.p. 87°-89° C.

Workup

  1. waitleft overnight
  2. extractionextracted with ether
  3. customThe product thus obtained
  4. customwas crystallised from diethylether

Sources & evidence

ORD record
ord-4d4da764b7ca493a80454e012df84e7d
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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