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

HRID 1425902Notes

Reaction equation

HRID 1425902 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-7bbf4dc4652d488d9bceabe59c4ad405
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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