Triethyl 2-fluoro-2-phosphonoacetate → HCID 86597851, compound

HRID 2180602Notes

Reaction equation

HRID 2180602 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=O)[CH3:18])[C:3]=1[O:20][CH3:21].[CH3:22][CH2:23][O:24][C:25]([CH:27](P(OCC)(OCC)=O)[F:28])=[O:26].C([Li])CCC>C1COCC1>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:15])[CH3:16])[C:6]=2[CH:5]=[C:4](/[C:17](/[CH3:18])=[C:27](/[F:28])\[C:25]([O:24][CH2:23][CH3:22])=[O:26])[C:3]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22490934HCID 22490934, compoundHCID 178418339Butyllithium

Product 1

HCID 86597851HCID 86597851, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(4-bromo-8-isopropyl-3-methoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-103, 358 mg, 1.02 mmol) and triethyl 2-fluoro-2-phosphonoacetate (0.83 μL, 4.08 mmol) were reacted with n-butyllithium (1.6 M in hexanes, 2.55 mL, 4.08 mmol) in THF to produce the title compound after purification by flash column chromatography (silica gel, 2% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-6a2b755a62734262be0bb85a626c8fe6
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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