Methanol → ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1662047Notes

Reaction equation

HRID 1662047 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][C:4]=1[CH3:14])=[O:2].CO.[BH4-].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C.O>[OH:2][CH2:1][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][C:4]=1[CH3:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59454108ethyl 5-formyl-1,4-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 59454025ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylateYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 5-formyl-1,4-dimethyl-1H-pyrrole-2-carboxylate (0.99 g) and methanol (10 ml) was added sodium borohydride (0.38 g) under ice-cooling, followed by stirring for 5 minutes under ice-cooling. To a reaction mixture was added a saturated aqueous ammonium chloride solution under ice-cooling, followed by stirring at room temperature for 0.5 hour. To the reaction mixture were added water and ethyl acetate, and the aqueous layer was separated and extracted with ethyl acetate. The organic layer was combined, washed with a saturated sodium bicarbonate solution and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to obtain ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylate (0.66 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. stirringby stirring at room temperature for 0.5 hour
  5. customthe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. washwashed with a saturated sodium bicarbonate solution and saturated brine in this order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c7b63308f5d74e49b665a7c9fdaa6c1c
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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