Tetraethyl methylenediphosphonate → HCID 10382970, compound

HRID 922315Notes

Reaction equation

HRID 922315 reaction equation
[H-].[Na+].[CH2:3]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])P(=O)(OCC)OCC.[CH2:20]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31](/[CH:32]=[CH:3]/[P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])=[CH:34][CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 10382970HCID 10382970, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To A 100 mL 2 necked RB flask charged with a suspension of NaH (0.14 g, 5.67 mmol) in THF (50 mL) under Nitrogen atmosphere was added tetraethyl methanediylbis(phosphonate) (1.63 g, 5.67 mmol) in THF drop wise at 0° C. This solution was stirred at the same temperature for 5 min followed by the addition of 4-(benzyloxy)benzaldehyde slowly. Reaction mixture was stirred at RT for 4 h. Excess NaH was quenched with ice and stirred for 5 min. Then the RM was diluted with ethyl acetate (50 mL) and the organic layer was washed with water (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as oil (1.6 g, yield: 98%). 1H NMR (300 MHz, CDCl3): δ 7.28-7.45 (m, 8H), 6.89-7.23 (d, 2H), 5.96-6.08 (t, 1H), 5.03 (s, 2H), 4.0-4.1 (m, 3H), 1.26-1.30 (t, 3H)

Workup

  1. customdrop wise at 0° C
  2. customReaction mixture
  3. stirringwas stirred at RT for 4 h
  4. customExcess NaH was quenched with ice
  5. stirringstirred for 5 min
  6. additionThen the RM was diluted with ethyl acetate (50 mL)
  7. washthe organic layer was washed with water (20 mL)
  8. dry with materialThe organic layer was dried over anhydrous Na2SO4
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b44f56c807614fff98d8c536d4c096e1
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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