Propargyl bromide → 4-(2-Furyl)-4-methoxy-1-butyne

HRID 1032498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1032498
[Br-].[CH2:2]([Al+2])[C:3]#[CH:4].[Br-].C(Br)C#C.[Al].CO[CH:14]([O:20][CH3:21])[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.O1CCCC1>[O:19]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:14]([O:20][CH3:21])[CH2:4][C:3]#[CH:2]

Komponenten

7

Edukt 4

HCID 7842Propargyl bromideHCID 5359268AluminumHCID 118154652-(Dimethoxymethyl)furanHCID 86744225Propargyl aluminum bromide

Produkt 1

HCID 147744234-(2-Furyl)-4-methoxy-1-butyne

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of propargyl aluminum bromide, prepared from 52.9 g of 80% propargyl bromide in toluene, 6.41 g of aluminum splutters activated with 70 mg of mercuric choride and 80 ml of tetrahydrofuran, was added dropwise a solution of 42.2 g of furfural dimethyl acetal [J. Org. Chem., 40, 1478 (1975)] in 30 ml of tetrahydrofuran during a 15 minute period while maintaining a temperature of. 25° to 30° C. The mixture was stirred for 20 minutes at 25° C., then partitioned with ether and ice-water. The organic layer was separated, washed with water, then aqueous sodium bicarbonate, finally with brine and dried. After evaporation the residue was distilled, giving 39.8 g of the desired compound, bp 68°-69° C. (11 mm).

Aufarbeitung

  1. temperaturewhile maintaining a temperature of
  2. custom25° to 30° C
  3. custompartitioned with ether and ice-water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialaqueous sodium bicarbonate, finally with brine and dried
  7. customAfter evaporation the residue
  8. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-b993ba9142e94eea8bd5cbcb62f1af6c
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04958037

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