Boron trifluoride → 2-(3-Methyl-1-pyrrolyl)phenol

HRID 1581792Notes

Reaction equation

HRID 1581792 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:4]=1)=O.C([BH3-])#N.[Na+].B(F)(F)F.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OC)(C)(C)C>[CH3:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:4]=1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 11608056HCID 11608056, compound

Product 1

HCID 227234482-(3-Methyl-1-pyrrolyl)phenolYield 11.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To 2-(3-formyl-1-pyrrolyl)phenol (2.9 g, 15.5 mmol) in 50 ml dry tetrahydrofuran are added sodium cyanoborohydride (1.94 g, 31 mmol) and boron trifluoride diethyletherate (5.7 ml, 47 mmol). The resulting solution is stirred for 3 hours at ambient temperature. Saturated sodium bicarbonate (100 ml) is added and the resulting mixture is stirred for 1 hour before extraction with t-butylmethylether. The organic layer is dried and concentrated and the residue is purified by chromatography (toluene/ethanol 9:1) to yield 2-(3-methyl-1-pyrrolyl)phenol (300 mg, 11%). This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield the title epoxide.

Workup

  1. customThe organic layer is dried
  2. concentrationconcentrated
  3. customthe residue is purified by chromatography (toluene/ethanol 9:1)

Sources & evidence

ORD record
ord-fa428e500cf34715b0b6f07a0deb37b7
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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