Hydrochloric Acid → Methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoate

HRID 399838Notes

Reaction equation

HRID 399838 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[N:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[OH:20])[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1)=[O:4].C(OCC)(=O)C.Cl>O1CCCC1.O>[OH:20][C:19]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 18945402Methyl 3-(2-formylpyrrol-1-yl)-4-hydroxybenzoate

Product 1

HCID 18945313Methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoateYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.46 g) was added to a solution of methyl 3-(2-formylpyrrol-1-yl)-4-hydroxybenzoate (3.0 g) in tetrahydrofuran (30 ml) and the mixture was stirred for 1 hour at ambient temperature. The reaction mixture was added to the mixture of ethyl acetate and water and adjusted to pH 7.5 with 6N-hydrochloric acid. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoate (2.54 g).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a010ead794d430fa13c2af3fe7cc041
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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