Potassium Carbonate → Methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate

HRID 2305629Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH:15](C)[CH2:16][C:17]([O:19][CH3:20])=[O:18].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][CH:15]([CH2:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH3:22])[CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-methoxy-4-nitrophenol (0.207 mg. 1.23 mmole) {Aldrich}, methyl 4-bromo-3-methylbutyrate(0.25 g. 1.35 mmole) and potassium carbonate (0.19 g. 1.35 mmole) in DMF (10 mL.) was heated and stirred at 80° C. for 8 hours. After cooling, the inorganics were filtered off, and the filtrate evaporated to dryness. The residue was dissolved in dichloromethane and washed twice with water. After drying (MgSO4) the solvent was evaporated off to yield an oil. The oil was purified by chromatography (Varian Megabondelut silica column) using a gradient of 100% dichloromethane to 20% ethyl acetate/dichloromethane to give methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate as an oil (90 mg. 29%) ms 284(M+)

Workup

temperaturewas heated
temperatureAfter cooling
filtrationthe inorganics were filtered off
customthe filtrate evaporated to dryness
dissolutionThe residue was dissolved in dichloromethane
washwashed twice with water
dry with materialAfter drying (MgSO4) the solvent
customwas evaporated off
customto yield an oil
customThe oil was purified by chromatography (Varian Megabondelut silica column)

Sources & evidence

ORD record: ord-567cb79db0824821a119fb0e7f4831ce
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441012B1

Reaction notes

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