Sodium borohydride → 1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethane-1,2-diol

HRID 2377007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377007
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:28])[CH2:26][OH:27])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH:25]([OH:28])[CH2:26][OH:27])(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 210993881-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]-2-hydroxyethanone

Produkt 1

HCID 210993891-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]-2-hydroxyethanone (Example 167, 20 mg, 0.05 mmol) and sodium borohydride (10 mg, 0.26 mmol) in methanol (2 mL) and dichloromethane (0.5 mL) was stirred at room temperature for 30 minutes. The reaction was quenched with water and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. δH (500 MHz, d6 DMSO): 8.04 (1H, d, J=7.9 Hz), 7.84-7.79 (4H, m), 7.74 (1H, d, J=7.7 Hz), 7.70-7.67 (3H, m), 7.53 (1H, t, J=7.3 Hz), 7.44 (1H, d, J=16.3 Hz), 7.29 (1H, d, J=16.4 Hz), 7.23 (2H, t, J=8.6 Hz), 5.36 (2H, s), 4.71 (1H, s), 3.32 (1H, s), 3.17 (1H, s).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2508b529ebb343109263ab25bca3d152
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468393B2

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