Acetic Anhydride → HCID 44185486, compound
Reaction equation
[F:1][CH:2]([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:12](OCC)(OCC)[O:13][CH2:14][CH3:15].C(OC(=O)C)(=O)C>>[CH2:14]([O:13]/[CH:12]=[C:4](/[C:3](=[O:10])[CH:2]([F:11])[F:1])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:15]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a freshly prepared solution of sodium ethoxide (prepared by addition of 1.11 g, 48.35 mmol Na metal in 8 mL EtOH) in EtOH was added a solution of ethyl difluoroacetate (5.0 g, 40.29 mmol) in EtOAc (9 mL) at rt and the reaction mixture was heated at 65° C. for 2 h. Then the reaction mixture was quenched with 1N HCl at rt and the pH was adjusted to 6-7. Then the reaction mixture was extracted with EtOAc and the organic layer was washed with water and brine, separated, dried, filtered and concentrated to afford 5.5 g of ethyl 4,4-difluoro-3-oxobutanoate which was taken to the next step without further purification. To a mixture of ethyl 4,4-difluoro-3-oxobutanoate (5.5 g, 33.11 mmol) and triethyl orthoformate (12 mL, 66.26 mmol) was added acetic anhydride (27.0 g, 265.0 mmol) and the reaction mixture was heated at 100° C. for 12 h. Then the reaction mixture was concentrated to afford 5.5 g of the title product which was taken to the next step without further purification.
Workup
- customwas taken to the next step without further purification
- concentrationThen the reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-803ad3fa427a415e9c8d6a7078efdaf5
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006257B2
Reaction notes
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