Acetone → Benzyl 2-(benzylsulfanyl)benzoate

HRID 11308

Reaktionsgleichung

Reaktionsgleichung von HRID 11308
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].N12CCCN=[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:30]C(C)=O>>[CH2:22]([O:9][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH2:30][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 4

HCID 180AcetoneHCID 54432-Mercaptobenzoic AcidHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 802018Benzyl 2-(benzylsulfanyl)benzoate

Versuchsvorschrift

A solution of thiosalicylic acid 1 (2.0 g, 13.0 mmol) in 13 mL of acetone was treated with 1,8-Diazabicyclo [5.4.0]undec-7-ene (7.8 mL, 52 mmol) and benzylbromide (6.2 mL, 52 mmol). The reaction was stirred at room temperature for 50 minutes. The mixture was concentrated under vacuum to remove the acetone. Water was added and the mixture was extracted with EtOAc (3X). The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid without purification.

Aufarbeitung

  1. concentrationThe mixture was concentrated under vacuum
  2. customto remove the acetone
  3. additionWater was added
  4. extractionthe mixture was extracted with EtOAc (3X)
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow solid
  10. customwithout purification

Quellen und Nachweise

ORD-Eintrag
ord-80e9b56178c6445892639d64b6cc2feb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098223B2

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