Acetic Anhydride → HCID 178472003, compound
Reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=1[F:18])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:19](OC(=O)C)(=O)C.C(OCC)(OCC)OCC.[NH2:36][C:37]([CH3:41])([CH3:40])[CH2:38][OH:39]>CCO.C(Cl)Cl>[OH:39][CH2:38][C:37]([NH:36]/[CH:19]=[C:3](/[C:2](=[O:1])[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=1[F:18])\[C:4]([O:6][CH2:7][CH3:8])=[O:5])([CH3:41])[CH3:40]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A stirred solution of commercially available ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propanoate (6) (15 g, 56.8 mmol), acetic anhydride (13.4 mL, 142 mmol) and triethyl orthoformate (14.1 mL, 18 mmol) was heated at 120° C. for 1.5 h. The mixture was concentrated in vacuo and dried under high vacuum for 5 hours. 10.1 g (31.5 mmol) of the crude product were dissolved in EtOH/DCM (30 mL) and cooled to 0° C. 2-Amino-2-methylpropan-1-ol (3.36 mL, 34.7 mmol) was added very slowly to this solution. After 30 minutes, the solvent was removed by evaporation and the product was freeze-dried to yield 7, as a yellow solid (11.9 g crude) that was used in the next step without further purification.
Workup
- concentrationThe mixture was concentrated in vacuo
- customdried under high vacuum for 5 hours
- customthe solvent was removed by evaporation
- customthe product was freeze-dried
- customto yield 7
- customas a yellow solid (11.9 g crude) that was used in the next step without further purification
Sources & evidence
- ORD record
- ord-3c86315d179b41149fa9b04559e8c3ba
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389514B2
Reaction notes
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