Propargyl alcohol → 1-(2-propynyl)-1H-pyrrole-2-carbonitrile
Reaction equation
[C:1]([C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1)#[N:2].[C:8]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=CC=C[CH:9]=1.C(O)C#C.N(C(OCC)=O)=NC([O-])=O>O1CCCC1>[CH2:13]([N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:1]#[N:2])[C:8]#[CH:9]Participants
Conditions
- Temperature
- 5 °C
Procedure
51.57 g of 2-cyano-pyrrol[prepared by the process of Can. J. Chem. Vol. 59, p. 2763 (1981)], 146.9 g of triphenylphosphine, and 43.95 g of propargyl alcohol were mixed together and 420 ml of tetrahydrofuran were added. The mixture was cooled at ±5° C., and over half an hour at 0° to 5° C., 97.5 g of ethyl azodicarboxylate were introduced. The temperature was allowed to return to ambient, and stirring was maintained for 18 hours. The solvent was evaporated under reduced pressure, and the crystallized residue was taken up in ethyl ether and filtered. After concentrating the filtrate, an oil was obtained which was chromatographed over silica. Elution with a hexane-ethyl acetate (7-3) mixture yielded 34 g of 1-(2-propynyl)-1H-pyrrole-2-carbonitrile.
Workup
- waitover half an hour at 0° to 5° C.
- temperaturewas maintained for 18 hours
- customThe solvent was evaporated under reduced pressure
- filtrationfiltered
- concentrationAfter concentrating the filtrate
- customan oil was obtained which
- customwas chromatographed over silica
- washElution with a hexane-ethyl acetate (7-3) mixture
Sources & evidence
- ORD record
- ord-6c3c6705b1c6407ca54baa756ba0c9df
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04798901
Reaction notes
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