Triethyl 2-fluoro-2-phosphonoacetate → HCID 86597858, compound

HRID 2180609Notes

Reaction equation

HRID 2180609 reaction equation
[Cl: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][CH2:21][CH3:22].[CH3:23][CH2:24][O:25][C:26]([CH:28](P(OCC)(OCC)=O)[F:29])=[O:27].C([Li])CCC>C1COCC1>[Cl: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](/[CH3:18])=[C:28](/[F:29])\[C:26]([O:25][CH2:24][CH3:23])=[O:27])[C:3]=1[O:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22490889HCID 22490889, compoundHCID 178418339Butyllithium

Product 1

HCID 86597858HCID 86597858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(4-chloro-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydronaphthalen-2-yl)-ethanone (Compound A-121, 0.23 g, 0.72 mmol) and triethyl 2-fluoro-2-phosphonoacetate (566 mg, 2.3 μmmol) were reacted with n-butyllithium (1.6 M in hexanes, 1.46 mL, 2.3 mmol) in THF to produce the title compound after purification by flash column chromatography (silica gel, 2% to 4% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-f3df9234e97e401a8c8c3952d7557c3a
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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