Iodoethane → Methyl 2-(4-t-butylphenyl)butanoate

HRID 380962Notes

Reaction equation

HRID 380962 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:26](I)[CH3:27]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH2:26][CH3:27])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 605629Methyl p-tert-butylphenylacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 10728413Methyl 2-(4-t-butylphenyl)butanoateYield 115.2%

Procedure

4 g (19 mmol) of methyl 4-tert-butylphenylacetate, 19.5 mL (1.0 M, 19 mmol) of lithium bis(trimethylsilyl)amide and 3.12 g (20 mmol) of ethyl iodide were reacted as described in Preparation 11 to yield 5.13 g of a brown oil. Chromatography, eluting with a gradient solvent of hexane to hexane/ethyl acetate 19:1 gave the title compound 2.35 g (53%).

Workup

  1. customas described in Preparation 11

Sources & evidence

ORD record
ord-666de0979c4f478fb2fab98834d013a3
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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