3-(3'-Hydroxyphenyl)propionic acid → HCID 57672487, compound

HRID 2101769Notes

Reaction equation

HRID 2101769 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].C([P+](CCCC)(CCCC)CCCC)CCC.Cl[CH2:32][C:33]1[CH:34]=[C:35]([C:42]2[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=2[F:50])[C:36]([CH:39]2[CH2:41][CH2:40]2)=[CH:37][CH:38]=1>C1COCC1>[CH:39]1([C:36]2[C:35]([C:42]3[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=3[F:50])=[CH:34][C:33]([CH2:32][O:1][C:2]3[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=3)=[CH:38][CH:37]=2)[CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)HCID 57672390HCID 57672390, compound

Product 1

HCID 57672487HCID 57672487, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3-hydroxyphenyl)-propionic acid (0.031 g, 0.186 mmol) (commercially available from Alfa, CAS No. 621-54-5) in THF (1 mL) was added tetrabutylphosphonium hydroxide (40 wt % solution in water) (0.27 g, 0.39 mmol). The mixture was then cooled in an ice bath to 0° C. After 10 minutes, 13.5 (0.055 g, 0.191 mmol) was added at 0° C. Upon complete addition, the reaction was allowed to warm to room temperature. After 44 hours, the solvent was removed under vacuum. The residue was diluted with water and acidified with 2M HCl to pH 2. The mixture was extracted with EtOAc. The layers were separated and the solvent was removed under vacuum to yield an oil that was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 65% EtOAc in hexanes) to yield a colorless film 13 (0.023 g, 28% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (1H, dd, J=8.0, 1.8 Hz), 7.31 (1H, d, J=2.0 Hz), 7.23 (1H, t, J=8.0 Hz), 7.10 (1H, m), 6.99 (1H, d, J=7.8 Hz), 6.90 (5H, m), 5.04 (2H, s), 3.82 (3H, s), 2.95 (2H, t, J=7.8 Hz), 2.72 (2H, m), 1.85 (1H, m), 0.87 (2H, m), 0.68 (2H, m).

Workup

  1. additionUpon complete addition
  2. temperatureto warm to room temperature
  3. waitAfter 44 hours
  4. customthe solvent was removed under vacuum
  5. additionThe residue was diluted with water
  6. extractionThe mixture was extracted with EtOAc
  7. customThe layers were separated
  8. customthe solvent was removed under vacuum
  9. customto yield an oil that
  10. customwas purified by flash chromatography (SiO2 gel 60, eluted with 0 to 65% EtOAc in hexanes)
  11. customto yield a colorless film 13 (0.023 g, 28% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (1H, dd, J=8.0, 1.8 Hz), 7.31 (1H, d, J=2.0 Hz), 7.23 (1H, t, J=8.0 Hz), 7.10 (1H, m), 6.99 (1H, d, J=7.8 Hz), 6.90 (5H, m), 5.04 (2H, s), 3.82 (3H, s), 2.95 (2H, t, J=7.8 Hz), 2.72 (2H, m), 1.85 (1H, m), 0.87 (2H, m), 0.68 (2H, m)

Sources & evidence

ORD record
ord-204cbfa43bcb4d9296dceaf76678a4f9
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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