1-Octanethiol → Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl ester

HRID 732194

Reaktionsgleichung

Reaktionsgleichung von HRID 732194
[F:1][C:2]([F:17])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCC>ClCCl>[F:1][C:2]([F:17])([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Komponenten

5

Edukt 3

HCID 81441-OctanethiolHCID 6451240Aluminum(III) ChlorideHCID 15487039Ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate

Produkt 1

HCID 22345522Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate (1.72 g, 7.05 mmol) synthesized according to the method described in Synthesis, vol. 13, pages 1917-1924, 2000 and aluminum chloride (2.82 g, 21.2 mmol) in dichloromethane (50 mL) was added dropwise 1-octanethiol (2.06 g, 14.1 mmol) and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was poured into ice water and stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=8:92-60:40) to give the title compound (0.90 g, yield 56%) as a colorless oil.

Aufarbeitung

  1. stirringstirred for 30 min
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=8:92-60:40)

Quellen und Nachweise

ORD-Eintrag
ord-b56224febd794d358837ce9b06f9d967
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585880B2

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