Triethylamine → Toluene 4-thiosulfonic acid S-[2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-phenyl] ester

HRID 356514

Reaktionsgleichung

Reaktionsgleichung von HRID 356514
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH2:33][O:34][CH3:35])[C:26]([CH3:36])=[CH:25][C:24]=1[SH:37])([CH3:22])([CH3:21])[CH3:20]>C(Cl)C(Cl)Cl.CCOC(C)=O>[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH2:33][O:34][CH3:35])[C:26]([CH3:36])=[CH:25][C:24]=1[S:37][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 187987002-Tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-benzenethiol

Produkt 1

HCID 53987067Toluene 4-thiosulfonic acid S-[2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-phenyl] ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 65741,1,2-TrichloroethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of tosyl bromide (21.0 g; 89.32 mmol), 50 mL of trichloroethane and 20 mL of NEt3 was cooled to 0° C. To this solution was added slowly a solution of 12.4 mmol of 2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-benzenethiol (prepared in Example AAAA) in 100 mL of trichloroethane. After 13 hours, the reaction mixture was diluted with EtOAc and washed with brine. The product was purified by flash silica gel chromatography, eluting with EtOAc:hexane (5:95, then switching to 3:7).

Aufarbeitung

  1. washwashed with brine
  2. customThe product was purified by flash silica gel chromatography
  3. washeluting with EtOAc:hexane (5:95

Quellen und Nachweise

ORD-Eintrag
ord-295045b58ba843feb787f80e37f1aa1e
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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