Tin tetrachloride → HCID 178527225, Verbindung

HRID 1872859

Reaktionsgleichung

Reaktionsgleichung von HRID 1872859
C([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][C:10]2(C)C)(C)(C)C.[O:17]1[CH2:21][CH2:20][CH:19]([C:22](Cl)=O)[CH2:18]1.[O:25]1CCC(C(O)=O)C1.C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.CCOCC>[O:25]=[SH:13]1([CH2:22][CH:19]2[CH2:20][CH2:21][O:17][CH2:18]2)[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH2:11][CH2:12]1

Komponenten

8

Edukt 5

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 107997308-Tert-butyl-4,4-dimethylthiochromaneHCID 14020412Tetrahydrofuran-3-carbonyl chloride

Produkt 1

HCID 178527225HCID 178527225, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 600 mg (2.56 mmol) of 8-tert-butyl-4,4-dimethyl-thiochromane and 0.38 g (2.84 mmol) of (+/-) tetrahydro-3-furoic acid chloride [which is prepared by reacting 1.5 g (12.9 mmol) (+/-) tetrahydro-3-furoic acid with 1.38 mL (15.5 mmol) oxalyl chloride in 40 mL benzene at 50° C. for 1 hour followed by concentration of the volatiles under reduced pressure] in 10 mL benzene at 0° C. is added 0.32 mL (2.73 mmol) tin tetrachloride. The reaction is allowed to stir 1 hour at 0° C. and is then diluted with ether and washed with water and sodium chloride. The product is purified by flash silica gel chromatography, eluting with 7:3 hexane:ethyl acetate to give 257 mg of 8-tert-butyl-4,4-dimethyl-6-(1-oxo-1-(3-tetrahydrofuryl)methylthiochromane.

Aufarbeitung

  1. customat 50° C.
  2. customfor 1 hour
  3. customat 0° C.
  4. washwashed with water and sodium chloride
  5. customThe product is purified by flash silica gel chromatography
  6. washeluting with 7:3 hexane

Quellen und Nachweise

ORD-Eintrag
ord-a22c8da7862d4f28964a4c084905d434
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06110960

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