Iodoethane → Ethyl 4-fluoro-3,3-dimethyl-2-oxobutanoate

HRID 520358Notes

Reaction equation

HRID 520358 reaction equation
[F:1][CH2:2][C:3]([CH3:10])([CH3:9])[C:4](=[O:8])[C:5]([OH:7])=[O:6].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:1][CH2:2][C:3]([CH3:10])([CH3:9])[C:4](=[O:8])[C:5]([O:7][CH2:12][CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 866900774-Fluoro-3,3-dimethyl-2-oxobutanoic acid

Product 1

HCID 86690078Ethyl 4-fluoro-3,3-dimethyl-2-oxobutanoateYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-3,3-dimethyl-2-oxobutanoic acid (2.3 g, 15.53 mmol) in DMF (30 mL) was added iodoethane (1.880 mL, 23.29 mmol) and K2CO3 (5.36 g, 38.8 mmol). The reaction mixture was stirred at rt for 18 h. The reaction mixture was diluted with EtOAc and stirred for 10 min. The solid was filtered. The filtration was partitioned between EtOAc and water. The organic phase was washed water, sat. NaCl, and concentrated. The residue was diluted with hexane (˜100 mL) and washed with water (2×30 mL), dried over MgSO4, filtered and concentrated to yield ethyl 4-fluoro-3,3-dimethyl-2-oxobutanoate (2.3 g).

Workup

  1. stirringstirred for 10 min
  2. filtrationThe solid was filtered
  3. filtrationThe filtration
  4. customwas partitioned between EtOAc and water
  5. washThe organic phase was washed water, sat. NaCl
  6. concentrationconcentrated
  7. additionThe residue was diluted with hexane (˜100 mL)
  8. washwashed with water (2×30 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-914b8ea25ceb421ab161d0da01eebf23
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…