4-Toluenesulfonyl chloride → 4-(Toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

HRID 1875757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875757
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Produkt 1

HCID 594606674-(Toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of 4-hydroxymethyl-cyclohexane carboxylic acid methyl ester (300 mg, 1.74 mmol; CAS Reg. No. 13380-85-3) in dichloromethane (10 ml) under nitrogen was added triethylamine (0.5 ml, 3.48 mmol) and p-toluenesulfonyl chloride (664 mg, 3.48 mmol; CAS Reg. No. 98-59-9) at 25° C. and the mixture was stirred for 16 h. The reaction mixture was evaporated under reduced pressure, and the crude product was purified by column chromatography over silica gel (ethyl acetate/n-hexane) to give the desired compound. Colorless powder (62%). MS (Turbo Spray): m/z=327.1 (M+H).

Aufarbeitung

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by column chromatography over silica gel (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6821d66075084931b41877d414b4f1ba
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309581B2

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