Beta-Propiolactone → 3-(4-Fluorophenylthio)propanoic acid

HRID 350773Notes

Reaction equation

HRID 350773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[C:9]1(=[O:13])[O:12][CH2:11][CH2:10]1.[H-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:11][CH2:10][C:9]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2365Beta-PropiolactoneHCID 24758Sodium hydrideHCID 677894-Fluorothiophenol

Product 1

HCID 27788893-(4-Fluorophenylthio)propanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

p-Fluorothiophenol (5 g, 40 mmol) and β-propiolactone (2.8 g, 40 mmol) were dissolved in THF (36 mL of freshly distilled) and then placed in an ice bath. 95% sodium hydride (1 g, 42.9 mmol) was added in small portions over 1 hour. The reaction was allowed to stir at 0° C. for 2 hours, then placed in the freezer overnight. The reaction was quenched with ice chips and then acidified with concentrated hydrogen chloride until a pH of 2. The product was extracted with ethyl acetate (1×200 mL) and dichloromethane (2×200 mL), dried (sodium sulfate) and concentrated to give 3-[(4-fluorophenyl)sulfanyl]propanoic acid (7.08 g, 89%). 1H NMR (CDCl3, 300 MHz): δ 7.42–7.35 (m, 2H), 7.02 (t, 2H, J=8.6 Hz), 4.35 (t, 1H, J=6.2 Hz), 3.10 (t, 2H, J=7.3 MHz), 2.63 (t, 2H, J=7.3 Hz) ppm.

Workup

  1. distillationof freshly distilled) and
  2. customthen placed in an ice bath
  3. customplaced in the freezer overnight
  4. customThe reaction was quenched with ice chips
  5. extractionThe product was extracted with ethyl acetate (1×200 mL) and dichloromethane (2×200 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4b1e5e683bf742bcbae77ac21721e07f
Source dataset
uspto-grants-2007_02
Patent number
US07183282B2

Reaction notes

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