Sodium Chloride → HCID 21842032, compound

HRID 1737287Notes

Reaction equation

HRID 1737287 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C[O-].[Na+].[C:25]([P:35](=[O:42])([O:39][CH2:40][CH3:41])[O:36][CH2:37][CH3:38])([P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH2:26].[Cl-].[NH4+].[Cl-].[Na+]>C(O)(C)C>[CH2:37]([O:36][P:35]([O:39][CH2:40][CH3:41])([CH:25]([P:27]([O:28][CH2:29][CH3:30])([O:31][CH2:32][CH3:33])=[O:34])[CH2:26][CH:2]([C:1]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:42])[CH3:38]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 84754Dibenzyl malonateHCID 10942334Sodium MethoxideHCID 11022954Tetraethyl vinylidene phosphonate

Product 1

HCID 21842032HCID 21842032, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Under a nitrogen atmosphere, dibenzyl malonate (1.71 g) was dissolved in isopropanol (10 ml) and sodium methoxide (27 mg) was suspended therein. A solution of tetraethyl ethenylidenebisphosphonate (1.51 g) in isopropanol (5 ml) was added dropwise thereto at room temperature and stirred for 2 hours. A saturated aqueous ammonium chloride solution (2.5 ml) and a saturated aqueous sodium chloride solution were added to the reaction mixture, followed by extraction (twice) with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by a silica gel column chromatography (chloroform:acetone=9:1 to 2:1) to obtain benzyl 4,4-bis(diethoxyphosphinoyl)-2-benzyloxycarbonylbutyrate (1.91 g, yield 65%).

Workup

  1. extractionfollowed by extraction (twice) with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by a silica gel column chromatography (chloroform:acetone=9:1 to 2:1)

Sources & evidence

ORD record
ord-b6082ee9615f40ad9dd7d077490be218
Source dataset
uspto-grants-1999_10
Patent number
US05962438

Reaction notes

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