Dichloromethane → 4-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylate

HRID 2084739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084739
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:15])(O)[CH:10]([CH3:13])[CH2:11][OH:12].C(N(CC)CC)C.ClCCl.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O>[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)([O:12][CH2:11][CH:10]([CH3:13])[CH:9]([OH:15])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:34])=[O:33]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 227346504-(2-Fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol

Produkt 1

HCID 120705744-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of 13.5 g (68.1 mmol) of 4-(2-fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol, 14.2 ml (21.3 mmol) of triethylamine, and 70 ml of dichloromethane was cooled with an ice bath and 13.0 g (68.1 mmol) of p-toluenesufonyl chloride was added to the mixture. After stirring overnight at room temperature, 100 ml of water was added thereto, followed by extraction 3 times each with 200 ml of dichloromethane, and the combined organic layer was dried with anhydrous sodium sulfate. After drying, the solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 21.1 g of the title compound as a colorless oil. (Yield: 88%)

Aufarbeitung

  1. temperaturewas cooled with an ice bath
  2. extractionfollowed by extraction 3 times each with 200 ml of dichloromethane
  3. dry with materialthe combined organic layer was dried with anhydrous sodium sulfate
  4. customAfter drying
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4e56efa2cda5482fb900e092ba09a00d
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06717016B2

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