Water → HCID 19083311, compound

HRID 483680Notes

Reaction equation

HRID 483680 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([O:20][CH3:21])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C(=O)C)[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].O.C(=O)(O)[O-].[Na+]>CO>[CH2:6]([O:5][P:4]([CH:9]([O:20][CH3:21])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19083318HCID 19083318, compound

Product 1

HCID 19083311HCID 19083311, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethyl-1-methoxy-1-(3-acetoxyphenyl)methanephosphonate from Example 8 (10.29 g., 32.56 mmol) was dissolved in methanol (35 ml). Water (5 ml), and sodium bicarbonate (5 g, 60 mmol) were then added with stirring. After 48 hours at room temperature, the reaction mixture was concentrated in vacuo to remove methanol. The residue was treated with 150 ml dichloromethane and washed with water (2×50 ml). The organic layer was rotory evaporated and pumped at high vacuum to yield 8.21 g. (93%) of the product as a light yellow, viscous oil. Spectral data (Tables 5 and 9) are in accordance with the structure: ##STR34##

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove methanol
  3. additionThe residue was treated with 150 ml dichloromethane
  4. washwashed with water (2×50 ml)
  5. customThe organic layer was rotory evaporated
  6. customto yield 8.21 g

Sources & evidence

ORD record
ord-fd5d1a987c134349889aa37dfd69b53e
Source dataset
uspto-grants-1993_07
Patent number
US05225584

Reaction notes

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