4-Toluenesulfonyl chloride → HCID 22799131, Verbindung

HRID 26992

Reaktionsgleichung

Reaktionsgleichung von HRID 26992
[CH3:1][C@H:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][C@@H:4]([OH:8])[C:5]#[C:6][CH3:7].[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21](O)=[O:22])([O-:17])=[O:16].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21]([O:8][C@H:4]([CH2:3][C@H:2]([CH3:1])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:5]#[C:6][CH3:7])=[O:22])([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 74333,5-Dinitrobenzoic acidHCID 22799132HCID 22799132, Verbindung

Produkt 1

HCID 22799131HCID 22799131, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

This compound was prepared similar to the method described in Example 44 from 4.22 g (21.6 mmol) of 6(R),10-dimethyl-undecan-2-yn-4(R)-ol, 4.58 g (21.6 mmol) of 3,5-dinitrobenzoic acid and 8.25 g (43.2 mmol) of p-toluenesulfonyl chloride in dry pyridine (total 55 ml) at 4° C. for 31/2 hr. It was worked up as described in Example 44 to give after recrystallization once from methanol 6.73 g (84.2%) of pure 6(R),10-dimethyl-undecan-2-yn-4(R)-ol 3,5-dinitrobenzoate, m.p. 90°-91°.

Aufarbeitung

  1. customThis compound was prepared similar to the method
  2. custom2 hr
  3. customto give
  4. customafter recrystallization once from methanol 6.73 g (84.2%) of pure 6(R),10-dimethyl-undecan-2-yn-4(R)-ol 3,5-dinitrobenzoate, m.p. 90°-91°

Quellen und Nachweise

ORD-Eintrag
ord-fcd36053abd6459491c51b1f75a61781
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151360

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