Lithium hydroxide, monohydrate → 1-(Carboxy)-1-(4-methoxybenzylthio)cyclopropane

HRID 375554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375554
[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][CH2:7]1)([O:3]CC)=[O:2].O.[OH-].[Li+]>C(O)C.O.O1CCCC1>[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1)([OH:3])=[O:2]

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 224002171-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

Produkt 1

HCID 224002161-(Carboxy)-1-(4-methoxybenzylthio)cyclopropaneAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (0.310 g, 1.16 mmol) in 95% ethanol (6 mL), water (3 mL), and tetrahydrofuran (6 mL). Treat with lithium hydroxide monohydrate (420 mg, 10 mmol). Stir at a gentle reflux for 6 hours and evaporate the solvent in vacuo. Add water (50 mL) and wash with ether (50 mL). Acidify the aqueous phase and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopropane as a pale yellow solid (266 mg).

Aufarbeitung

  1. temperaturea gentle reflux for 6 hours
  2. customevaporate the solvent in vacuo
  3. washAdd water (50 mL) and wash with ether (50 mL)
  4. extractionextract into methylene chloride (50 mL)
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5506c48621e742ceb5f59e574819f963
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486513

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