Triethylamine → Methyl 1-((acetylthio)methyl)cyclopropaneacetate

HRID 249048

Reaktionsgleichung

Reaktionsgleichung von HRID 249048
OC[C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4]1.C(N([CH2:16][CH3:17])CC)C.[CH3:18][S:19](Cl)(=O)=O.C([O-])(O)=[O:24].[Na+].S([O-])(=O)(=O)C>C(Cl)Cl.CN(C=O)C>[C:16]([S:19][CH2:18][C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5]1)(=[O:24])[CH3:17]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium Bicarbonate2×HCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester

Produkt 1

HCID 53482060Methyl 1-((acetylthio)methyl)cyclopropaneacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of the alcohol of Step 10 (28.2 g, 0.20 mol) and triethylamine (82 mL, 0.59 mol) in dichloromethane (1L) cooled to -40° C. was added methanesulfonyl chloride (43.5 mL, 0.3 mol). The reaction mixture was warmed to -10° C. for 20 min and then an aqueous solution of NaHCO3 was added. The product was extracted with CH2Cl2, washed with brine and dried over Na2SO4. A portion of this mesylate (0.053 mol) was then dissolved in DMF (180 mL) and cooled to 0° C. Freshly prepared cesium thiol acetate (J. Org. Chem., 51, 3664, (1986)) (22 g, 0.11 mol) was added and the mixture was stirred overnight at r.t. The reaction mixture was poured into an aqueous solution of NaHCO3 and extracted with Et2O. The organic phases were washed with brine and dried over Na2SO4. The residual oil was then purified by flash chromatography with 10:1 hexane:EtOAc to yield 7.5 g, 70%, of the title compound.

Aufarbeitung

  1. extractionThe product was extracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. temperaturecooled to 0° C
  5. extractionextracted with Et2O
  6. washThe organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe residual oil was then purified by flash chromatography with 10:1 hexane
  9. customEtOAc to yield 7.5 g, 70%

Quellen und Nachweise

ORD-Eintrag
ord-f0cec03e94b74c9d8e2de5b44b762c09
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212180

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