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

HRID 975048Notes

Reaction equation

HRID 975048 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-1977898ce141453c851abd2a68955c73
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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