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

HRID 1764791ノート

反応式

HRID 1764791 の反応式
[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

参加物

5

反応物 3

HCID 2365Beta-PropiolactoneHCID 24758Sodium hydrideHCID 677894-Fluorothiophenol

生成物 1

HCID 27788893-(4-Fluorophenylthio)propanoic acid収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9a4867c90c1843a7b384e5572afe5c19
出典データセット
uspto-grants-2007_06
特許番号
USRE039680E1

反応ノート

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