Dimethylformamide → HCID 54060285, compound
Reaction equation
CN(C)[CH:3]=[O:4].[C:6](=[O:9])([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(OO[CH2:17][C:18]([F:21])([F:20])[F:19])(=O)=O.C(=O)([O-])O.[Na+].[OH:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][C:44]=1O)[O:41][C:40]([CH3:47])([CH3:46])[CH2:39]C2=O>>[F:19][C:18]([F:21])([F:20])[CH2:17][O:34][C:35]1[CH:44]=[C:43]2[C:42](=[CH:37][C:36]=1[O:9][CH2:6][C:18]([F:21])([F:20])[F:19])[O:41][C:40]([CH3:39])([CH3:46])[CH2:47][C:3]2=[O:4]Participants
6
Conditions
- Temperature
- 120 °C
Procedure
In 100 ml of N,N-dimethyl-formamide 4.2 g (20 millimoles) of 6,7-dihydroxy-2,2-dimethyl-4-chromanone are dissolved under nitrogen whereupon 8.3 g (60 millimoles) of potassium carbonate and 11.5 g (45 millimoles) of trifluoroethoxy tosylate are added. The reaction mixture is stirred at 120° C. for 10 hours, poured onto 200 ml of crushed ice, 100 ml of saturated sodium hydrogen carbonate solution are added and the mixture is extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 100 ml of water each, dried over anhydrous sodium sulfate and the solvent is removed. The residue is crystallized from ethanol. Thus 4.8 g of the desired compound are obtained, yield 65%. Mp.: 92°-93° C.
Workup
- additionare added
- additionare added
- extractionthe mixture is extracted three times with 50 ml of carbon tetrachloride each
- washThe organic phase is washed twice with 100 ml of water each,
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent is removed
- customThe residue is crystallized from ethanol
Sources & evidence
- ORD record
- ord-c16cbc80471f45119802b2aab5054e89
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04968819
Reaction notes
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