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

HRID 1862155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862155
[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 (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 MM (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-f786dce0d7714a88a1a7f5f958f3a46f
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534524B1

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