Methanol → [1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol

HRID 2181551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181551
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=[O:19])(=[O:12])=[O:11].[Li+].[BH4-].CO>C1COCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][OH:19])(=[O:12])=[O:11]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 218774321-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrole-2-carbaldehyde

Produkt 1

HCID 21877558[1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrole-2-carbaldehyde (2.77 g, 10 mmol) in THF (0.100 ml) was treated with LiBH4 (0.44 g, 20 mmol) at rt. The resulting solution was held at rt for 1 h. MeOH (10 ml) was then added, and the resulting mixture mixture was poured into brine (600 ml), and extracted with EtOAc (3×200 ml). The combined organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified on silica gel column to yield [1-(2,4,6-Trimethyl-benzenesulfonyl)-1H-pyrrol-2-yl]-methanol as a light brown oil (2.43 g, 87%). 1H NMR (CDCl3) δ 7.17 (dd, 1H, J=3.3, 1.8 Hz), 6.99 (s, 2H), 6.28-6.23 (m, 1H), 6.18 (t, 1H, J=3.3 Hz), 4.42 (s, 2H), 2.50 (s, 6H), 2.30 (s, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×200 ml)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil was then purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-9e88414996bd4e75ac91203c05adc62b
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06891044B2

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