Dimethyl methylphosphonate → HCID 86620239, compound

HRID 639946Notes

Reaction equation

HRID 639946 reaction equation
[CH3:1][P:2](=[O:7])([O:5]C)[O:3][CH3:4].C([Li])C[CH2:10][CH3:11].[CH3:13]CCCCC.[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=2)=[CH:31][C:28]=1[CH2:29]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:4]([O:3][P:2]([CH2:1][CH2:29][C:28]1[CH:31]=[C:32]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=2)[CH:33]=[CH:34][C:27]=1[O:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:7])[O:5][CH2:10][CH3:11])[CH3:13]

Participants

5

Reactant 3

HCID 12958Dimethyl methylphosphonateHCID 68420425HCID 68420425, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86620239HCID 86620239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of dimethyl methylphosphonate (0.7 mL) in THF (8.2 mL) was added 2.44 M n-butyllithium/n-hexane solution (2.6 mL) at −78° C., and the reaction mixture was stirred for 0.5 hr at −78° C. A solution of [2-benzyloxy-5-(4-ethylbenzyl)benzyl chloride (1.50 g) in THF (8.2 mL) was added to the mixture at −78° C., and the reaction mixture was stirred for 2 hr at −78° C.˜−10° C. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=2/3) to give the title compound (0.74 g) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred for 2 hr at −78° C.˜−10° C
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=2/3)

Sources & evidence

ORD record
ord-8608e20c4be04f6699dbc7955ed8af53
Source dataset
uspto-grants-2010_04
Patent number
US07691898B2

Reaction notes

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