Water → HCID 22261369, compound

HRID 1610044Notes

Reaction equation

HRID 1610044 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=CC=1.[P:7](Cl)(Cl)(Cl)=[O:8].[C:12]([C:16]1[C:17]([CH3:38])([CH3:37])[CH2:18][O:19][C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[O:29][N:28]=2)=[C:23]([OH:36])[CH:22]=1)([CH3:15])([CH3:14])[CH3:13].[CH2:39]([C:42]#[N:43])[CH2:40][OH:41].[OH2:44]>ClCCl>[C:42]([CH2:39][CH2:40][O:41][P:7](=[O:8])([O:44][CH2:4][CH2:5][C:6]#[N:1])[O:36][C:23]1[CH:22]=[C:21]([C:20]2[O:19][CH2:18][C:17]([CH3:38])([CH3:37])[C:16]=2[C:12]([CH3:15])([CH3:13])[CH3:14])[CH:26]=[CH:25][C:24]=1[C:27]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[O:29][N:28]=1)#[N:43]

Participants

7

Reactant 5

HCID 962WaterHCID 1049Pyridine2×HCID 8011HydracrylonitrileHCID 24813Phosphorus oxychlorideHCID 135850838HCID 135850838, compound2×

Product 1

HCID 22261369HCID 22261369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a nitrogen atmosphere, 1.84 ml (22.8 mmol) of pyridine was added to 30 ml of dichloromethane at 0° C., and further, 1.33 ml (14.3 mmol) of phosphorus oxychloride was added, followed by stirring for 15 minutes. To this reaction solution, a solution having 4-t-butyl-5-[4-(5-trifluoromethyl-3-isoxazolyl)-3-hydroxyphenyl]-3,3-dimethyl-2,3-dihydrofuran (compound 13)) (1.44 g, 3.78 mmol) dissolved in dichloromethane (12 ml), was dropwise added, followed by stirring at 0° C. for 2 hours. Further, the reaction solution was gradually returned to room temperature and stirred for 1 day. The reaction solution was again cooled to 0° C., and 3.68 ml (45.5 mmol) of pyridine was added. Further, 3.20 ml (47.3 mmol) of ethylene cyanohydrin was added, and the mixture was gradually returned to room temperature and stirred for 1 day. The reaction solution was put into pure water (50 ml) and extracted with ethyl acetate (50 ml). The aqueous layer was again extracted with ethyl acetate (50 ml), and the extract was put together with the previous organic layer, followed by washing with pure water (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain the desired phosphoric acid 5-(3-t-butyl-4,4-dimethyl-4,5-dihydrofuran-2-yl)-2-(5-trifluoromethylisoxazol-3-yl)phenylester bis-(2-cyanoethyl)ester (compound (15)) as a slightly yellow oily substance (2.10 g, 3.70 mmol, 98.1%).

Workup

  1. additionwas dropwise added
  2. stirringby stirring at 0° C. for 2 hours
  3. customwas gradually returned to room temperature
  4. stirringstirred for 1 day
  5. customwas gradually returned to room temperature
  6. stirringstirred for 1 day
  7. extractionextracted with ethyl acetate (50 ml)
  8. extractionThe aqueous layer was again extracted with ethyl acetate (50 ml)
  9. washby washing with pure water (100 ml×3)
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c6358e12a58b482b8e6009229ca78f71
Source dataset
uspto-grants-2006_01
Patent number
US06982336B2

Reaction notes

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