Ozone → N-(3-Hydroxy-1-phenylpropyl)-N-methylbenzenesulfonamide

HRID 860164

Reaktionsgleichung

Reaktionsgleichung von HRID 860164
[O:1]=[O+][O-].[CH3:4][N:5]([CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][CH:17]=C)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[BH4-].[Na+]>CO>[OH:1][CH2:17][CH2:16][CH:15]([N:5]([CH3:4])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 69447982N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide

Produkt 1

HCID 69444505N-(3-Hydroxy-1-phenylpropyl)-N-methylbenzenesulfonamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Ozone was bubbled through a solution of the product of Step 1 (1.0 g, 3.3 mmol) in MeOH (50 mL) at −78° C. for 30 min, then after appearance of a pale blue colour, the reaction was purged with N2 for several minutes and NaBH4 (245 mg, 6.6 mmol) was added. The resulting solution was allowed to warm to RT and stirred for a further 15 min at RT. The reaction was quenched by the addition of NH4Cl solution (10 mL) and then concentrated under reduced pressure. H2O (50 mL) was added and then extracted with EtOAc (100 ml and 50 mL). The combined organic extracts were dried (MgSO4) and then concentrated under reduced pressure to yield the alcohol (0.94 g, 93%). 1H NMR (CDCl3, 400 MHz) δ 7.81 (2H, d, J=7.2 Hz), 7.65–7.45 (3H, m), 7.20–7.13 (3H, m), 6.93 (2H, d, J=7.5 Hz), 5.25 (1H, dd, J=9.1, 6.3 Hz), 3.90–3.80 (1H, m), 3.74–3.59 (1H, m), 2.63 (3H, s), 2.13–1.98 (2H, m).

Aufarbeitung

  1. customafter appearance of a pale blue colour, the reaction was purged with N2 for several minutes
  2. customThe reaction was quenched by the addition of NH4Cl solution (10 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionH2O (50 mL) was added
  5. extractionextracted with EtOAc (100 ml and 50 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5199f67ea3c74e9b95806897c31fed38
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153868B2

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