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

HRID 1862155Notes

Reaction equation

HRID 1862155 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f786dce0d7714a88a1a7f5f958f3a46f
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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