Ethanol → 2,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-one

Reaction equation

O[C:2]([CH3:13])([CH3:12])[C:3]#[C:4][C:5]([C:7]1[N:8]=[CH:9][S:10][CH:11]=1)=[O:6].C(NCC)C.C([OH:21])C>>[CH3:12][C:2]1([CH3:13])[C:3](=[O:21])[CH:4]=[C:5]([C:7]2[N:8]=[CH:9][S:10][CH:11]=2)[O:6]1

Participants

Reactant 3

HCID 702Ethanol2×

HCID 8021Diethylamine

HCID 59354863HCID 59354863, compound

Product 1

HCID 593548052,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-one

Procedure

To a stirred solution of 4-hydroxy-4-methyl-1-(thiazol-4-yl) pent-2-yn-1-one (0.1 g, 0.53 mmol) in ethanol (1 mL) was added diethyl amine (0.057 mL, 0.59 mmol) in EtOH (0.5 mL) dropwise at RT and the reaction mixture was stirred for additional 45 min. Then the EtOH was removed, diluted with EtOAc (10 mL), washed with water (5 mL), brine (5 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford 2, 2-dimethyl-5-(thiazol-4-yl) furan-3(2H)-one (0.1 g) as an oil.