HCID 57799869, compound → HCID 57799540, compound

HRID 2101096Notes

Reaction equation

HRID 2101096 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12]>O=S(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12])[C:15](=[O:17])[CH2:14][CH2:13]2

Participants

3

Reactant 1

HCID 57799869HCID 57799869, compound

Product 1

HCID 57799540HCID 57799540, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
45 °C

Procedure

The mixture of 3-[3-Fluoro-4-(2-methoxy-ethoxy)-phenyl]-propionic acid (16 g) in SOCl2 (50 ml) was refluxed for 4 hours. The mixture was evaporated, the residue was dissolved in CS2 (100 ml), and then AlCl3 (20 g) was added. The mixture was heated at 45° C. for 4 hours. 200 ml of ice-water was added to the cooled mixture and the mixture was stirred for another 1 hour. The mixture was extracted by ethyl acetate (300 ml×3). The product was purified by flash column chromatography using ethyl acetate:PE=5:1 as eluent. LC-MS: m/e 225 (MH+).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in CS2 (100 ml)
  4. additionAlCl3 (20 g) was added
  5. addition200 ml of ice-water was added to the cooled mixture
  6. extractionThe mixture was extracted by ethyl acetate (300 ml×3)
  7. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-a715b30c0787431882890d2d03bc11cb
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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