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m-Chloroperbenzoic acid → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester

HRID 2214104
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2214104
[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:16]1[CH:21]=[CH:20][C:19](SC)=[C:18]([Cl:24])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2([O:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:7]1.Cl[C:27]1C=C(C=CC=1)C(OO)=O.C(=O)(O)[O-].[Na+].[S:42](=[O:45])(O)[O-:43].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([S:42]([CH3:27])(=[O:45])=[O:43])=[C:18]([Cl:24])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2([O:11][CH2:12][CH2:13][CH2:14][O:15]2)[CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 67482163HCID 67482163, Verbindung

Produkt 1

HCID 674820872-(3-Chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.18 g, 3.07 mmol) in methylene chloride (8 mL) cooled to 0° C. was slowly treated with a mixture of 3-chloroperoxybenzoic acid (˜70%, 1.51 g based on 70%, 6.13 mmol) and sodium bicarbonate (1.03 g, 12.26 mmol) in methylene chloride (8 mL). The thick reaction mixture was diluted with methylene chloride (8 mL) and was then allowed to warm to 25° C., where it was stirred for 4 h. The reaction mixture was diluted with methylene chloride (200 mL) and water (200 mL). The organic phase was cooled down to 0° C. and then slowly treated with a saturated aqueous sodium bisulfite solution (200 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL), and a saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.22 g, 95%) as a colorless oil: EI-HRMS m/c calcd for C19H25ClO6S (M)+ 416.1060 found 416.1054.

Aufarbeitung

  1. temperatureThe organic phase was cooled down to 0° C.
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL)
  3. dry with materiala saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5185c75bb05540b09f50c2fadfdc0e70
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07105671B2

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