Pyridine → (R)-2-butanol 4-bromobenzenesulfonate

HRID 609581

Reaktionsgleichung

Reaktionsgleichung von HRID 609581
[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.N1C=CC=CC=1.ClCCl>CN(C)C1C=CN=CC=1.O>[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:15])(=[O:5])=[O:14])=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7396p-Bromobenzenesulfonyl chlorideHCID 84682(-)-2-Butanol

Produkt 1

HCID 131721473(R)-2-butanol 4-bromobenzenesulfonateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 8.2 g of (R)-(-)2-butanol, 31.5 g of 1-bromo-4-benzenesulfonyl chloride, 1.0 g of N,N-dimethyl-4-pyridinamine, 55.5 ml of pyridine and 293 ml of dichloromethane was stirred for 3 days at room temperature. After the addition of water, stirring was continued for 1 hour. The reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water, dried, filtered and evaporated in vacuo. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 11.5 g (35.6%) of (R)-2-butanol 4-bromobenzenesulfonate (ester) (interm. 3).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. washThe reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d5986d069af7448ea5744b080474cb62
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998413

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