Carbon Dioxide → HCID 86757669, compound

HRID 2269808Notes

Reaction equation

HRID 2269808 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(=O)=O.[CH2:14]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])P(=O)(OCC)OCC.[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O>O1CCCC1.C(OCC)(=O)C>[CH3:40][O:39][C:37]([C:36]1[CH:41]=[CH:42][C:33](/[CH:31]=[CH:14]/[P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])=[CH:34][CH:35]=1)=[O:38]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 15294Methyl 4-FormylbenzoateHCID 15455Tetraethyl methylenediphosphonateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 86757669HCID 86757669, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (17 ml) is diluted with anhydrous tetrahydrofuran (81 ml) under a nitrogen atmosphere and dry ice cooling, and then a solution of tetraethyl methylenebis(phosphonate) (4.6 g) in anhydrous tetrahydrofuran (8 ml) is added dropwise thereto. The mixture is stirred under dry ice cooling for 30 minutes, and then a solution of methyl 4-formylbenzoate (2.64 g) in anhydrous tetrahydrofuran (12 ml) is added dropwise thereto. The mixture is stirred under dry ice cooling for 1.5 hours and further under ice cooling for 2.5 hours. Ethyl acetate is added to the reaction mixture. The organic layer is washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting precipitate is filtered off to give 4.1 g (86%) of diethyl (E)-2-[4-(methoxycarbonyl)phenyl]vinylphosphonate as crystals.

Workup

  1. stirringThe mixture is stirred under dry ice cooling for 1.5 hours and further under ice cooling for 2.5 hours
  2. washThe organic layer is washed with water and saturated brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe resulting precipitate is filtered off

Sources & evidence

ORD record
ord-132103f8488448ba867fc27728c12c86
Source dataset
uspto-grants-2001_12
Patent number
US06329547B1

Reaction notes

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