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

HRID 629943노트

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HRID 629943 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39f00b24ac414ab3a54c9cc403b2627a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315530B2

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