Ethanol → 1-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol

HRID 2805

Reaction equation

HRID 2805 reaction equation
O1C=CC(C2O[C:8]([C:12]([C:14]3[O:18][C:17](C4C=COC=4)=[N:16][C:15]=3[CH3:24])=[O:13])=[C:9]([CH3:11])N=2)=C1.[CH3:25][Li].[CH2:27]([OH:29])C.[Cl-].[Na+]>C(OCC)C>[O:29]1[CH:11]=[CH:9][C:8]([C:12]([C:14]2[O:18][CH:17]=[N:16][C:15]=2[CH3:24])([OH:13])[CH3:25])=[CH:27]1

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 541705673-Furyl-4-methyl-5-oxazolyl ketoneHCID 178418348HCID 178418348, compound

Product 1

HCID 97941531-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Furyl-4-methyl-5-oxazolyl ketone (1 g) in dry diethylether (15 ml) at -70° C. under a nitrogen atmosphere was treated dropwise with methyllithium (1.5M solution in diethylether, 4.1 ml). After 45 minutes the reaction mixture was allowed to warm to room temperature and ethanol (2 ml) was added. The mixture was poured into saturated aqueous sodium chloride and extracted with dichloromethane. Chromatography and crystallisation then gave 1-(3-furyl)-1-(4-methyl-5-oxazolyl)ethanol identical to the material obtained in (a) above.

Workup

  1. extractionextracted with dichloromethane
  2. customChromatography and crystallisation

Sources & evidence

ORD record
ord-c3b3ce4ed08846c8b1f2907496e08f51
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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