Cesium carbonate → HCID 22737360, compound

HRID 51080Notes

Reaction equation

HRID 51080 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:21]=[CH:20][C:19]=1[O:30][CH2:31][CH2:32][CH2:33]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:27])([F:29])[F:28])[CH:21]=[CH:20][C:19]=1[O:30][CH2:31][CH2:32][CH2:33][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylateHCID 227373543-Bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether

Product 1

HCID 22737360HCID 22737360, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a 40 ml DMF solution of ethyl 7-hydroxy-chromane-2-carboxylate (1.81 g, 8.15 mmol) and 3-bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether (3.4 g, 9.8 mmol) was added cesium carbonate (3.2 g, 9.8 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on slica gel eluting with 20% AcOEt/hexanes to give the title compound 3.23 g (81%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and 2N hydrochloric acid
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on slica gel
  9. washeluting with 20% AcOEt/hexanes

Sources & evidence

ORD record
ord-c41b1a77a6704e59a2c298e1a3132e1f
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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