4-Methylbenzenesulfonyl fluoride → HCID 20492938, Verbindung

HRID 434551

Reaktionsgleichung

Reaktionsgleichung von HRID 434551
[Cl-].[CH3:2][S+:3]([CH3:6])([CH3:5])=[O:4].[H-].[Na+].C[SH+](C)=O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](F)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[F:24][P-:25]([F:30])([F:29])([F:28])([F:27])[F:26].[H+]>O1CCCC1>[F:24][P-:25]([F:30])([F:29])([F:28])([F:27])[F:26].[CH3:2][S+:3]([CH3:6])([CH2:5][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])=[O:4]

Komponenten

7

Edukt 5

HCID 99654-Methylbenzenesulfonyl fluorideHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 16211447Hexafluorophosphoric acidHCID 22345572HCID 22345572, Verbindung

Produkt 1

HCID 20492938HCID 20492938, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dimethylsulphoxonium methylide was prepared by the method described by Corey and Chaykovsky, loc. cit., from trimethylsulphoxonium chloride (25.7 parts) by treatment with sodium hydride (6.7 parts) in dry tetrahydrofuran. This ylide was converted into dimethylsulphoxonium p-toluenesulphonylmethylide by reaction with p-toluenesulphonyl fluoride (17.4 parts) using the method described by Truce and Madding, loc. cit. The toluenesulphonylmethylide was neutralised by the addition of 65% aqueous hexafluorophosphoric acid (49.5 parts) over 15 minutes, followed by concentration of the solution. The white solid which precipitated was filtered off, washed with water, and dried under vacuum to give 20 parts of the desired product (VI, R=p--CH3C6H4, R6 =H, R7 =R8 =CH3, q=t=1, Zt- =PF6-), mpt. 174°-5° C.; NMR (acetone -d6) 2.50 (s-3H), 4.23 (s-6H), 6.20 (s-2H), 7.5-8.2 (m-4H); IR (KBr disc) 3020, 3000, 2930, 2920, 1590, 1400, 1330, 1300, 1250, 1160, 1030, 940, 840, 750 cm-1 ; UV (ethanol) λmax 255 nm (data for product recrystallised from methanol).

Aufarbeitung

  1. customDimethylsulphoxonium methylide was prepared by the method
  2. customThe white solid which precipitated
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-82e9a440a9374e538782f44612445930
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04398014

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