1-(Isopropylsulfonyl)-4-methylbenzene → Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate

HRID 850906

Reaktionsgleichung

Reaktionsgleichung von HRID 850906
C([Li])CCC.[CH:6]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:8])[CH3:7].[CH3:19][O:20][CH:21]([O:28][CH3:29])/[CH:22]=[CH:23]/[C:24]([O:26][CH3:27])=[O:25].P(O)(O)([O-])=O.[Na+]>O1CCCC1.CCCCCC>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([C:6]([CH3:7])([CH3:8])[CH:22]([CH:21]([O:28][CH3:29])[O:20][CH3:19])[CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 8167921-(Isopropylsulfonyl)-4-methylbenzeneHCID 5371699Methyl 4,4-dimethoxybut-2-enoateHCID 23672064Monosodium phosphateHCID 178418339Butyllithium

Produkt 1

HCID 12850320Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

3.4 ml of a 1.95 M of butyllithium per liter of hexane were added at -70° C. to a mixture of 1.24 g of p-tolyl isopropyl sulfone in 13 ml of tetrahydrofuran and after stirring the mixture for 15 minutes, a solution of 1 g of methyl (E) 4,4-dimethoxy-2-butenoate in 20 ml of tetrahydrofuran was slowly added thereto. The mixture was stirred at -20° C. for one hour and was then poured into an aqueous monosodium phosphate solution. The mixture was extracted with methylene chloride and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an ether-petroleum ether (b.p. =40° to 70° C.) mixture to obain 1.1 g of methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethyl-pentanoate melting at 110° C.

Aufarbeitung

  1. stirringThe mixture was stirred at -20° C. for one hour
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe organic phase was dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with an ether-petroleum ether (b.p. =40° to 70° C.) mixture

Quellen und Nachweise

ORD-Eintrag
ord-19c3af42bef64026a408ca3417872471
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382037

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