Triethyl 2-fluoro-2-phosphonoacetate → HCID 69732052, compound

HRID 2180604Notes

Reaction equation

HRID 2180604 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)[CH:18]([CH3:20])[CH3:19])[C:3]=1[O:22][CH2:23][CH3:24].[CH3:25][CH2:26][O:27][C:28]([CH:30](P(OCC)(OCC)=O)[F:31])=[O:29].C([Li])CCC>C1COCC1>[Br:1][C:2]1[C:11]2[C:10]([CH3:12])([CH3:13])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:15])[CH3:16])[C:6]=2[CH:5]=[C:4](/[C:17](/[CH:18]([CH3:19])[CH3:20])=[C:30](/[F:31])\[C:28]([O:27][CH2:26][CH3:25])=[O:29])[C:3]=1[O:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 69732452HCID 69732452, compoundHCID 178418339Butyllithium

Product 1

HCID 69732052HCID 69732052, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-methyl-propan-1-one (Compound A-111, 234 mg, 0.60 mmol) and triethyl 2-fluoro-2-phosphonoacetate (576 mg, 2.38 mmol) were reacted with n-butyllithium (1.6 M in hexanes, 1.48 mL, 2.38 mmol) in THF to produce the title compound as a clear oil after purification by flash column chromatography (silica gel, 2% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-7826c083bf504396a00f86cb223074c0
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…