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Hydrochloric Acid → (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanol

HRID 1380681
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1380681
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][OH:29].N1C=CC=C[CH:33]=1.Cl>C(Cl)Cl>[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([O:22][CH3:23])=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][C@:27]([CH3:31])([OH:30])[CH2:28][O:29][S:1]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:9][C:10]=1[CH3:33])(=[O:2])=[O:3]
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11129761(S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

Produkt 1

HCID 86740735(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluenesulphonyloxy-2-butanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

237 mg of tosyl chloride and 350 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol were dissolved in 1 ml of methylene chloride. 0.180 ml of pyridine was then added dropwise at 0° C. and the mixture was left to stand at 0° C. for 1 hour and then at room temperature for 16 hours. 1 g of ice and 0.3 ml of concentrated hydrochloric acid were thereupon added. The mixture was then extracted with methylene chloride and the extracts were dried and concentrated. There were obtained 511 mg (95%) of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluylsulphonyloxy-2-butanol. [α]D20 +1.2° (c=2.6% in chloroform).

Aufarbeitung

  1. waitthe mixture was left
  2. waitat room temperature for 16 hours
  3. extractionThe mixture was then extracted with methylene chloride
  4. customthe extracts were dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7ae02965084d468fbef361338b84b949
Quelldatensatz
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04582919

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