Potassium Carbonate → HCID 22874127, compound

HRID 1684542Notes

Reaction equation

HRID 1684542 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12](=[O:21])[O:13][C@@H:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C@@H:7]1[CH2:6][CH2:5]2.Br[CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:15]1([C@H:14]2[C@@H:7]3[CH2:6][CH2:5][C:4]4[C:9]([N:8]3[C:12](=[O:21])[O:13]2)=[CH:10][CH:11]=[C:2]([O:1][CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:3]=4)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 22874129HCID 22874129, compound

Product 1

HCID 22874127HCID 22874127, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.65 g (2.3 mmol) of cis-(±)-7-hydroxy-3-phenyl-3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolin-1-one in 15 ml of dimethylformamide are added 0.66 g (3.5 mmol) of 1-bromo-4,4,4-trifluorobutane and 0.64 g (4.6 mmol) of potassium carbonate. The mixture is heated for 4 hours at 90° C. and is then diluted with ethyl acetate and washed with water. The organic phase is then dried over sodium sulphate and concentrated under reduced pressure, and the residue is chromatographed on a column of silica, with cyclohexane containing 20% of ethyl acetate. After trituration in diisopropyl ether, 0.60 g of product is obtained.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is then dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is chromatographed on a column of silica, with cyclohexane containing 20% of ethyl acetate

Sources & evidence

ORD record
ord-81b912243dbe4849aaa53b79e0c95022
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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