Triethyl 2-fluoro-2-phosphonoacetate → HCID 86597857, compound

HRID 2180608Notes

Reaction equation

HRID 2180608 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:18](=O)[CH3:19])[C:3]=1[O:21][CH:22]([CH3:24])[CH3:23].[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]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([C:14]([CH3:16])([CH3:15])[CH3:17])[C:6]=2[CH:5]=[C:4](/[C:18](/[CH3:19])=[C:30](/[F:31])\[C:28]([O:27][CH2:26][CH3:25])=[O:29])[C:3]=1[O:21][CH:22]([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22490920HCID 22490920, compoundHCID 178418339Butyllithium

Product 1

HCID 86597857HCID 86597857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(4-bromo-8-tert-butyl-3-isopropoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-115, 143 mg, 0.36 mmol) and triethyl 2-fluoro-2-phosphonoacetate (352 mg, 1.46 mmol) were reacted with n-butyllithium (1.6 M in hexanes, 0.91 mL, 1.46 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-102cf056fcff496a91832a9f1c967dd6
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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