Lithium diisopropylamide → HCID 86597841, compound

HRID 2180568Notes

Reaction equation

HRID 2180568 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([C:15](=O)[CH3:16])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[C:5]([CH:18]([CH3:20])[CH3:19])=[CH:4][CH2:3]1.[CH3:22][CH2:23][O:24][C:25]([CH:27](P(OCC)(OCC)=O)[F:28])=[O:26].C([N-]C(C)C)(C)C.[Li+]>C1COCC1>[F:28]/[C:27](=[C:15](/[C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:1])([CH3:21])[CH2:3][CH:4]=[C:5]2[CH:18]([CH3:19])[CH3:20])=[CH:10][C:9]=1[O:12][CH2:13][CH3:14])\[CH3:16])/[C:25]([O:24][CH2:23][CH3:22])=[O:26]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22491007HCID 22491007, compound

Product 1

HCID 86597841HCID 86597841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(4,4-dimethyl-6-ethoxy-1-isopropyl-3,4-dihydronaphthalen-7-yl)ethanone (Compound A-24, 240 mg, 0.840 mmol) and triethyl 2-fluoro-2-phosphonoacetate (0.51 mL, 2.52 mmol) were reacted with lithium diisopropylamide (2.60 mmol) in THF (2 mL) to produce the title compound after purification by flash column chromatography (silica gel, 97:3 hexane/ethyl acetate).

Sources & evidence

ORD record
ord-616803406a7643909defaf73ba455192
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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