Abstract
1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.
| Original language | English |
|---|---|
| Pages (from-to) | 843-846 |
| Number of pages | 4 |
| Journal | Bulletin of the Academy of Sciences of the USSR Division of Chemical Science |
| Volume | 18 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1 Apr 1969 |
| Externally published | Yes |
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- Chemistry(all)
Cite this
Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole. / Shvartsberg, M. S.; Vasilevskii, S. F.; Sagdeev, R. Z.; Kotlyarevskii, I. L.
In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 18, No. 4, 01.04.1969, p. 843-846.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole
AU - Shvartsberg, M. S.
AU - Vasilevskii, S. F.
AU - Sagdeev, R. Z.
AU - Kotlyarevskii, I. L.
PY - 1969/4/1
Y1 - 1969/4/1
N2 - 1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.
AB - 1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.
UR - http://www.scopus.com/inward/record.url?scp=34250487853&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34250487853&partnerID=8YFLogxK
U2 - 10.1007/BF00907056
DO - 10.1007/BF00907056
M3 - Article
VL - 18
SP - 843
EP - 846
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 0568-5230
IS - 4
ER -