Methyl iodide → Ethyl 2-(2-naphthyl)propanoate

HRID 1167208Notes

Reaction equation

HRID 1167208 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:17][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 256821Ethyl 2-naphthylacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 15676675Ethyl 2-(2-naphthyl)propanoateYield 108.7%

Procedure

5 g (23 mmol) of ethyl 2-naphthylacetate, 23.3 mL (1.0 M, 23 mmol) of lithium bis(trimethylsilyl)amide, and 1.5 mL (24 mmol) of methyl iodide were reacted as described in Preparation 11 to yield 5.71 g of a dark oil. Chromatography eluting with a solvent gradient of hexanes to hexanes/ethyl acetate 19:1 gave the title compound 2.85 g (54%).

Workup

  1. customas described in Preparation 11

Sources & evidence

ORD record
ord-62228db40332485e8e811ac11c4a3dd6
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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