Boron trifluoride etherate → 3-(2-propynyl)-5-hydroxymethyl-2-(3H)-thiazolone

HRID 1085208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1085208
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[CH:9])[CH:5]=[C:4]([C:10](OCC)=[O:11])[S:3]1.B(F)(F)F.CCOCC.[H-].C([Al+]CC(C)C)C(C)C.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[CH:5]=[C:4]([CH2:10][OH:11])[S:3][C:2]1=[O:1])[C:8]#[CH:9]

Komponenten

7

Edukt 5

HCID 8000Boron trifluoride etherateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5462222PotassiumHCID 14457166HCID 14457166, VerbindungHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 144571623-(2-propynyl)-5-hydroxymethyl-2-(3H)-thiazoloneAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 8.44 g of the product of Step B in 100 ml of toluene was cooled to -65° C. to -70° C. and 5.6 g of boron trifluoride etherate were added. The mixture was stirred for 30 minutes and 200 ml of a 1.2M solution of diisobutyl aluminium hydride in toluene were introduced over 2 hours 15 minutes. Stirring was carried out for a further 30 minutes and the mixture was poured into 1.5 l of a M solution of potassium and sodium tartrate. After stirring for one hour and decanting, extraction was carried out with ethyl acetate. The extracts were washed with water saturated with sodium chloride, dried and brought to dryness. The residue was chromatographed and elution with a hexane-chloroform-acetone mixture (6-2-2) yielded. 2.33 g of the expected product melting at 97° to 98° C.

Aufarbeitung

  1. stirringStirring
  2. waitwas carried out for a further 30 minutes
  3. stirringAfter stirring for one hour
  4. customdecanting
  5. extractionextraction
  6. washThe extracts were washed with water saturated with sodium chloride
  7. customdried
  8. customThe residue was chromatographed
  9. washelution with a hexane-chloroform-acetone mixture (6-2-2)
  10. customyielded

Quellen und Nachweise

ORD-Eintrag
ord-85bc89c436ea4c20910a8c5ca5e96a62
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008281

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