Water → HCID 67072583, Verbindung

HRID 1948147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948147
[CH:1]1([CH2:4][C:5]2([CH:15]=O)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[CH3:17][C:18]([S:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].O>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH:1]1([CH2:4][C:5]2([CH:15]=[N:23][S:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])[CH2:6][CH2:7][C:8]3([O:9][CH2:10][CH2:11][O:12]3)[CH2:13][CH2:14]2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 866563378-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

Produkt 1

HCID 67072583HCID 67072583, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The crude aldehyde was dissolved in tetrahydrofuran (40 mL) and 2-methyl-2-propanesulfinamide (1.81 g, 14.9 mmol, 1.1 eq.) and titanium(IV) ethoxide (4.27 mL, 20.3 mmol, 1.5 eq.) were added. The resulting mixture was stirred for 5 h under reflux and 16 h at room temperature, before being treated with water (10 mL) and filtered through celite. The filter cake was washed with ethyl acetate, the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.90 g of the title compound (19). Rt=1.58 min (Method B). Detected mass: 328.3 (M+H+).

Aufarbeitung

  1. filtrationfiltered through celite
  2. washThe filter cake was washed with ethyl acetate
  3. customthe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-909d78b107ad44cbb988c506077796e1
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399482B2

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