Ketone, 2,4-dimethylpyrrol-3-yl methyl → HCID 18470692, compound

HRID 2228611Notes

Reaction equation

[C:1]([C:4]1[C:8]([CH3:9])=[CH:7][NH:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl>CN(C=O)C>[C:1]([C:4]1[C:8]([CH3:9])=[CH:7][N:6]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[C:5]=1[CH3:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-acetyl-2,4-dimethyl-1H-pyrrole (commercially available from Aldrich Chem. Co. Inc., 1.50 g, 10.6 mmol) in DMF (40 mL) was added NaH (60% oil dispersion, 0.85 g, 21.2 mmol) at room temperature under nitrogen. After stirring for 30 minutes at room temprature the resulting suspension was cooled to 0° C. and added 2-(trimethylsilyl)ethoxymethyl chloride (3 mL, 15.9 mmol). The reaction mixture was warm to room temperature and stirred for 3 hours. The mixture was quenched with aqueous saturated NaHCO3 solution, and the whole extracted with diethyl ether (100 mL×2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, concentrated iii vaciio. Chromatographic purification of the crude product eluting ethyl acetate-hexane (1:10) gave the subtitle product (2.32 g, 82% yield).

Workup

temperatureThe reaction mixture was warm to room temperature
stirringstirred for 3 hours
customThe mixture was quenched with aqueous saturated NaHCO3 solution
extractionthe whole extracted with diethyl ether (100 mL×2)
washThe combined organic layers were washed with brine (50 mL)
dry with materialdried over MgSO4
concentrationconcentrated iii vaciio
customChromatographic purification of the crude product
washeluting ethyl acetate-hexane (1:10)

Sources & evidence

ORD record: ord-b4795aecd4e242b0ba45ed5dc439e289
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417202B1

Reaction notes

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