Methyl iodide → 2-Benzo[1,3]dioxol-5-YL-propanoic acid methyl ester

HRID 442673Notes

Reaction equation

[Li+].[CH3:2]C([N-]C(C)C)C.[CH2:9]1[O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:12][C:11]=2[O:10]1.CI.[NH4+].[Cl-]>C1COCC1>[CH2:9]1[O:17][C:16]2[CH:15]=[CH:14][C:13]([CH:18]([CH3:2])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][C:11]=2[O:10]1

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of LDA in THF (60 mL) was added methyl 3,4-methylenedioxyphenylacetate (2 g, 10.3 mmol) at -78° C. and the solution was warmed to -15° C. for 45 min. MeI (4.39 g, 30.9 mmol) was added and the reaction was warmed to room temperature for 16 h. The reaction mixture was then poured to a separatory funnel containing NH4Cl (80 mL) and the product was extracted with EtOAc (2×150 mL) and dried over Na2SO4. The crude product obtained by removal of the solvent was purified by flash chromatography to give the product as a colorless solid (1.36 g , 63%). 1H NMR (CDCl3) 6.75 (m, 3H), 5.95 (s 2H), 3.67 (s, 3H), 3.66 (m, 1H), 1.46 (d, J=7.4, 3H).

Workup

temperaturethe reaction was warmed to room temperature for 16 h
additionThe reaction mixture was then poured to a separatory funnel
extractionthe product was extracted with EtOAc (2×150 mL)
dry with materialdried over Na2SO4
customThe crude product obtained by removal of the solvent
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-91981f7473ca4d988f59dc211f1779b3
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891871

Reaction notes

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