Ethanol → 5-(4-Chlorophenyl)-2,2-dimethylfuran-3(2H)-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[C:9]#[C:10][C:11](O)([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(NCC)C.C([OH:23])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:15][C:11]([CH3:12])([CH3:13])[C:10](=[O:23])[CH:9]=2)=[CH:6][CH:7]=1Participants
4
Procedure
To a stirred solution of 1-(4-chlorophenyl)-4-hydroxy-4-methylpent-2-yn-1-one (2.4 g, 10.70 mmol) in ethanol (20 mL), a solution of diethyl amine (1.34 mL, 12.90 mmol) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 30 min. The ethanol was then removed and the mixture was diluted with EtOAc (50 mL). The combined organic layers were then washed with water (10 mL), and brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(4-chlorophenyl)-2,2-dimethylfuran-3(2H)-one (2.1 g) as a light green gummy oil.
Workup
- customThe ethanol was then removed
- additionthe mixture was diluted with EtOAc (50 mL)
- washThe combined organic layers were then washed with water (10 mL), and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-53fdd54ae0b7452eacd9c820b6eef09e
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071595B2
Reaction notes
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