Sodium borohydride → 4-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl alcohol

HRID 11894

Reaktionsgleichung

Reaktionsgleichung von HRID 11894
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15])(=[O:5])=[O:4].[BH4-].[Na+]>C1COCC1>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[O:14][CH3:15])(=[O:4])=[O:5]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 219768714-(N,N-Dimethylsulfamoyl)-3-methoxybenzaldehyde

Produkt 1

HCID 685585254-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl alcoholAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of OBS02011 (5.5 g, 21.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.88 g, 23.33 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The organic layer was washed with brine (2×200 mL), dried (Na2SO4) and filtered. Concentration in vacuo of the combined filtrates gave OBS02014 as a pale yellow oil (5.12 g, 92%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.18; 1H-NMR (270 MHz, CDCl3)=2.44 (1H, bs, OH), 2.92 (6H, s), 3.84 (3H, s), 4.60 (2H, s), 6.85 (1H, dd, J=2.2, 8.4), 6.97 (1H, d, J=1.8), 7.25 (1H, d, J=8.1). 4-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl chloride (OBS02016)

Aufarbeitung

  1. customquenched with water (CARE!!)
  2. filtrationfiltered through a Celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionre-dissolved in DCM (200 mL)
  5. washThe organic layer was washed with brine (2×200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationConcentration in vacuo of the combined filtrates

Quellen und Nachweise

ORD-Eintrag
ord-c11cc9676ab94e19a6703c7d9987902e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098343B2

Verknüpfte Notizen

Wird geladen…