Lithium diisopropylamide → HCID 86597844, compound

HRID 2180569Notes

Reaction equation

HRID 2180569 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:20])([CH3:19])[CH2:7][C:8](C(=O)C)=[C:9]2[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:21][CH2:22][CH2:23][CH3:24].[CH3:25][CH2:26][O:27][C:28]([CH:30](P(OCC)(OCC)=O)[F:31])=[O:29].[CH:40]([N-]C(C)C)(C)[CH3:41].[Li+]>C1COCC1>[F:31]/[C:30](=[C:40](/[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:19])([CH3:20])[CH2:7][CH:8]=[C:9]2[C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:4][C:3]=1[O:21][CH2:22][CH2:23][CH3:24])\[CH3:41])/[C:28]([O:27][CH2:26][CH3:25])=[O:29]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22490966HCID 22490966, compound

Product 1

HCID 86597844HCID 86597844, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in General Procedure F-1, 1-(7-bromo-4,4-dimethyl-6-propoxy-1-tert-butyl-3,4-dihydronaphthalen-yl)ethanone (Compound A-39, 34 mg, 0.11 mmol) and triethyl 2-fluoro-2-phosphonoacetate (0.17 mL, 0.86 mmol) were reacted with lithium diisopropylamide (0.86 mmol) in THF (2 mL) to produce the title compound as a yellow oil after purification by flash column chromatography (silica gel, 97:3 hexane:ethyl acetate).

Sources & evidence

ORD record
ord-0e6d959ed91c4105819894c549e6c6f0
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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