Pyridine → 2-Isopropyl-4-trifluoromethylsulfonyloxy-benzyl acetate

HRID 24263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24263
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=[O:5])=[O:4].[C:20](Cl)(=[O:22])[CH3:21].N1C=CC=CC=1>C(Cl)Cl>[C:20]([O:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][S:3]([C:2]([F:18])([F:1])[F:19])(=[O:4])=[O:5])=[CH:8][C:9]=1[CH:15]([CH3:17])[CH3:16])(=[O:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 225688934-Hydroxymethyl-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate2×

Produkt 1

HCID 187407082-Isopropyl-4-trifluoromethylsulfonyloxy-benzyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 4-hydroxymethyl-3-isopropylphenyl 1,1,1-trifluoromethanesulfonate (Intermediate 149, 190.0 mg, 0.64 mmol) in 5 mL CH2Cl2 was added acetyl chloride (75.0 mg, 0.96 mmol) and pyridine(101.0 mg, 1.38 mmols). After stirring for 3 hours at 25° C. the reaction was quenched by the addition of H2O and the resulting mixture extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound, 182 mg (84%), was isolated from the residual oil by column chromatography (5-10% EtOAc—hexanes) as a colorless oil.

Aufarbeitung

  1. customwas quenched by the addition of H2O
  2. extractionthe resulting mixture extracted with EtOAc
  3. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b5f23c000fd44a5962e150845024967
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855512B2

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