Dimethyl Sulfoxide → HCID 12816936, compound

HRID 472494

Reaction equation

HRID 472494 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].IC.[CH3:17]S(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:1][O:2][C:3](=[O:14])[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])[CH3:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 520464Methyl 2-(2-nitrophenyl)acetate

Product 1

HCID 12816936HCID 12816936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottom flask was charged with (2-nitro-phenyl)-acetic acid methyl ester (4.22 g, 21.6 mmol) (prepared as described in Organic Letters, 2009, 11, 1345-1348), iodomethane (2.8 mL, 45 mmol) and dry dimethyl sulfoxide (20 mL). Cesium carbonate (18 g, 56 mmol) was added and the mixture was stirred at room temperature under an atmosphere of nitrogen for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with water (2×30 mL), saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered and evaporated. 2-(2-Nitro-phenyl)-propionic acid methyl ester was isolated as a red oil (3.24 g, 71%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.93 (d, J=8.1 Hz, 1H), 7.60 (t, J=7.6 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 4.32 (q, J=7.0 Hz, 1H), 3.67 (s, 3H), 1.61 (d, J=7.0 Hz, 3H). MS=232 (MH)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic layers were washed with water (2×30 mL), saturated aqueous sodium chloride (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8a168fe4e74f48409d186127174607a2
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Linked notes

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