Dimethylformamide → Methyl (1R,2R)-2-(4-nitrophenyl)cyclopropanecarboxylate

HRID 922192Notes

Reaction equation

HRID 922192 reaction equation
CN([CH:4]=[O:5])C.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18](O)=[O:19])=[CH:11][CH:10]=1)([O-:8])=[O:7].C([O-])([O-])=O.[K+].[K+].CI>O>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18]([O:5][CH3:4])=[O:19])=[CH:13][CH:14]=1)([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 11736165Methyl (1R,2R)-2-(4-nitrophenyl)cyclopropanecarboxylateYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL RB flask fitted with magnetic stirrer was charged with 120 mL of DMF. To the stirred solvent was added (1R,2R)-2-(4-nitrophenyl)cyclo propane carboxylic acid (15 g, 72 mmol), K2CO3 (29 g, 217 mmol) and methyl iodide (5.5 mL, 86 mmol), stirred at RT for 8 h. The RM was poured into water (100 mL) and extracted with ethyl acetate (150 mL×2). The organic layer was washed with saturated NaHCO3 solution (50 mL), water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow color liquid (14 g, yield: 87.9%). MS (ESI, 120 eV): m/z=206.1 (M−H)+.

Workup

  1. customTo a 500 mL RB flask fitted with magnetic stirrer
  2. extractionextracted with ethyl acetate (150 mL×2)
  3. washThe organic layer was washed with saturated NaHCO3 solution (50 mL), water (50 mL) and saturated brine solution (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-67cdffc0d3e14bcdb5bfea72841faa58
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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