Water → (RS)-ethyl 2-(4-nitrophenyl)-heptanoate

HRID 394939Notes

Reaction equation

HRID 394939 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 123351-IodopentaneHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 86584487(RS)-ethyl 2-(4-nitrophenyl)-heptanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of ethyl 4-nitrophenylacetate dissolved in 20 ml of dimethylformamide was treated with 3.12 g of cesium carbonate and 0.68 ml of iodopentane. The mixture was stirred at room temperature for 18 hours. The mixture was poured onto 50 ml of iced water and the resulting mixture was extracted with two portions of 50 ml ether. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes), yielding a pale yellow oil. 1H NMR (CDCl3): 8.18 (d, J=8.6 Hz, 2H), 7.49 (d, J=8.8 Hz, 2H), 4.25-4.00 (m, 2H), 3.64 (t, J=7.7 Hz, 1H), 2.20-2.00 (m, 1H), 1.85-1.70 (m, 1H), 1.45-1.15 (m, 6H), 1.22 (t, J=7.2 Hz, 3H), 0.90-0.80 (m, 3H).

Workup

  1. extractionthe resulting mixture was extracted with two portions of 50 ml ether
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes)
  5. customyielding a pale yellow oil

Sources & evidence

ORD record
ord-168860cae44943499b9ff6fbc10b483b
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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