Water → cis-4-Tert-butyloxy-cyclopent-2-enol

HRID 2393896

Reaktionsgleichung

Reaktionsgleichung von HRID 2393896
[C:1]([O:5][C@@H:6]1[CH2:10][C@H:9]([O:11]C(=O)C)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].O.C(Cl)(Cl)Cl>C1COCC1.CO.O>[C:1]([O:5][C@@H:6]1[CH2:10][C@H:9]([OH:11])[CH:8]=[CH:7]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6212ChloroformHCID 168937Lithium hydroxide, monohydrateHCID 11074363(-)-Acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester

Produkt 1

HCID 11789450cis-4-Tert-butyloxy-cyclopent-2-enolAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Dissolve (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (90 mg, 0.45 mmol, prepared in example 14) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (23.7 mg) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column) to provide the title compound (71 mg, quantitative yield, 76% ee) as a pale yellow oil, [α]20D =+14.6°, (c 1.03, chloroform).

Aufarbeitung

  1. additiondilute
  2. extractionextract with tert-butyl methyl ether
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography (silica gel, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column)

Quellen und Nachweise

ORD-Eintrag
ord-915b45c62abc4ec0a786dd3ec144a16a
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808112

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