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

HRID 629943ノート

反応式

HRID 629943 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39f00b24ac414ab3a54c9cc403b2627a
出典データセット
uspto-grants-2016_04
特許番号
US09315530B2

反応ノート

読み込み中…