Sodium Iodide → Diethyl (1,1-difluoro-3-(2-(4-formyl-3-methoxyphenoxy)ethoxy)propyl)phosphonate

HRID 629943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629943
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])([F:28])[F:27]>CN(C=O)C.O.CCOC(C)=O>[F:28][C:26]([P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])([F:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 58166526Diethyl 3-(2-bromoethoxy)-1,1-difluoropropylphosphonate

Produkt 1

HCID 86667770Diethyl (1,1-difluoro-3-(2-(4-formyl-3-methoxyphenoxy)ethoxy)propyl)phosphonateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-hydroxy-2-methoxybenzaldehyde (1 equiv.) in DMF (0.25 M) was added cesium carbonate (2 equiv.), sodium iodide (0.20 equiv.) and diethyl (3-(2-bromoethoxy)-1,1-difluoropropyl)phosphonate (1.2 equiv.) (described in ref. 88, Ex 7 Step 1). The reaction mixture was stirred at 100° C. for 3 h, after which it was allowed to cool to room temperature. The resulting mixture was then diluted with water and EtOAc. This mixture was transferred to a separatory funnel and washed with water three times. The organic layer was then separated, dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-5% MeOH/DCM to provide the title compound (79%) as a solid.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThis mixture was transferred to a separatory funnel
  3. washwashed with water three times
  4. customThe organic layer was then separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customthe volatiles were removed in vacuo
  7. customThe resulting residue was purified by a COMBIFLASH™ system

Quellen und Nachweise

ORD-Eintrag
ord-39f00b24ac414ab3a54c9cc403b2627a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315530B2

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