Triethyl 2-fluoro-2-phosphonoacetate → HCID 86597838, compound

HRID 2180567Notes

Reaction equation

HRID 2180567 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].C([Li])CCC.[CH2:21]([O:23][C:24]1[C:25]([C:36](=O)[CH3:37])=[CH:26][C:27]2[CH:28]=[CH:29][CH2:30][C:31]([CH3:35])([CH3:34])[C:32]=2[CH:33]=1)[CH3:22]>C1COCC1>[CH2:21]([O:23][C:24]1[C:25](/[C:36](/[CH3:37])=[C:6](/[F:7])\[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:26][C:27]2[CH:28]=[CH:29][CH2:30][C:31]([CH3:35])([CH3:34])[C:32]=2[CH:33]=1)[CH3:22]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22491033HCID 22491033, compoundHCID 178418339Butyllithium

Product 1

HCID 86597838HCID 86597838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triethyl 2-fluoro-2-phosphonoacetate (0.61 g, 2.50 mmol) in THF (5 mL) at −78° C. was added n-butyllithium (1.6 M in hexane, 1.6 mL, 2.5 mmol). After 10 min, a solution of 1-(3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-25, 122 mg, 0.50 mmol) in THF (2 mL) was added and the reaction was stirred for 6 b while warming gradually to room temperature. The reaction was then quenched with aqueous NH4Cl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes) to give the title compound as a colorless oil.

Workup

  1. customThe reaction was then quenched with aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a74b2e333544444c82237739730d7b82
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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