Tetrahydrofuran → 1,3-Diphenyl-2-propyn-1-one

HRID 1757503

Reaktionsgleichung

Reaktionsgleichung von HRID 1757503
C([N-]C(C)C)(C)C.[Li+].O1CCCC1.[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CON(C)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1CCCCC1>[C:26]1([C:25](=[O:32])[C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 569575N-Methoxy-N-methylbenzamideHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 976371,3-Diphenyl-2-propyn-1-oneAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

Place lithium diisopropylamide (10 mL of a 1.5M solution in cyclohexane) and tetrahydrofuran (40 mL) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, phenylacetylene (1.65 mL, 15 mmol). Remove the cooling bath and stir for 30 minutes as room temperature. Cool the yellow solution to 0° C. and add, by dropwiseaddition, N-methoxy-N-methylbenzamide (3.04 mL, 20 mmol). Remove the cooling bath and stir for 30 minutes at room temperature. Pour onto ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Purify by silica gel chromatography (2% ethyl acetate/hexane) then purify further by distillation (2X) to yield 1.9 g of the title compound; bp 210° C. in vacuo.

Aufarbeitung

  1. customRemove the cooling bath
  2. temperatureCool the yellow solution to 0° C.
  3. customRemove the cooling bath
  4. stirringstir for 30 minutes at room temperature
  5. additionPour onto ethyl ether and water
  6. customseparate the organic phase
  7. dry with materialdry (MgSO4)
  8. filtrationFilter
  9. customevaporate the solvent in vacuo
  10. customto yield an oil
  11. customPurify by silica gel chromatography (2% ethyl acetate/hexane)
  12. distillationthen purify further by distillation (2X)

Quellen und Nachweise

ORD-Eintrag
ord-0cfb4af12318410b87fbc81c781bb8d2
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446068

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