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

HRID 1258361Notes

Reaction equation

HRID 1258361 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

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 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.

Workup

  1. customThen the EtOH was removed
  2. additiondiluted with EtOAc (10 mL)
  3. washwashed with water (5 mL), brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65e8d1e0e3fb4b24888a70820690d309
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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