Water → HCID 86584490, compound

HRID 394942Notes

Reaction equation

HRID 394942 reaction equation
[CH3:1][C:2]([CH3:24])=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[CH3:24][C:2]1([CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=2)[NH:6][C:4](=[O:5])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 86584489HCID 86584489, compound

Product 1

HCID 86584490HCID 86584490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of (RS)-ethyl 2-[4-(3,3-dimethylacrylamido)-phenyl]-heptanoate was dissolved in 10 ml of methylene chloride and treated with 1.2 g of aluminium chloride. The mixture was heated to reflux for 6 hours. The mixture was poured onto 25 ml of iced water and then was extracted with two portions of 25 ml of methylene chloride. The combined extracts were washed with two portion of 25 ml of saturated aqueous sodium bicarbonate solution and one portion of 25 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes). 1H NMR (CDCl3): 8.92 (br. s, 1H), 7.21 (d, J=1.9 Hz, 1H), 7.13 (dd, J=8.1, 1.9 Hz, 1H), 6.78 (d, J=8.1 Hz, 1H), 4.20-4.00 (m, 2H), 3.48 (t, J=7.7 Hz, 1H), 2.48 (s, 2H), 2.10-1.90 (m, 1H), 1.80-1.65 (m, 1H), 1.35-1.15 (m, 6H), 1.33 (s, 3H), 1.32 (s, 3H), 1.22 (t, J=7.1 Hz, 3H), 0.86 (t, J=6.6 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionwas extracted with two portions of 25 ml of methylene chloride
  4. washThe combined extracts were washed with two portion of 25 ml of saturated aqueous sodium bicarbonate solution and one portion of 25 ml of saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cbd0a16b0a994263834b79f6b9d35da5
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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