Water → Ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate

HRID 866770Notes

Reaction equation

HRID 866770 reaction equation
[CH:1]([C:3]1[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:10])[N:6]([CH3:9])[C:7]=1[CH3:8])=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:10])[N:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13425563Ethyl 4-formyl-1,2,5-trimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 13051083Ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 10.9 g of ethyl 4-formyl-1,2,5-trimethylpyrrole-3-carboxylate in 40 ml of methanol is added dropwise under nitrogen 5.6 g of sodium borohydride in methanol while maintaining the reaction temperature below 50° C. after total addition the reaction mixture is stirred at ambient temperature for 4 hours, then 90 ml of water introduced and the reaction mixture saturated with potassium carbonate and extracted with ether. The combined ether extracts are dried and concentrated in vacuo leaving a yellow solid which is recrystallized from cyclohexane to give ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate, mp 184°-186° C.

Workup

  1. temperaturewhile maintaining the reaction temperature below 50° C.
  2. additionafter total addition the reaction mixture
  3. extractionthe reaction mixture saturated with potassium carbonate and extracted with ether
  4. dry with materialThe combined ether extracts are dried
  5. concentrationconcentrated in vacuo
  6. customleaving a yellow solid which
  7. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-4100ff82fd5e43d8a8cad61ca321a35c
Source dataset
uspto-grants-1978_07
Patent number
US04101559

Reaction notes

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