Water → HCID 10749418, compound

HRID 1420559Notes

Reaction equation

HRID 1420559 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]1[CH:12]=[O:13].O.C([O-])([O-])=O.[K+].[K+]>CO>[OH:13][CH2:12][C:5]1[N:4]([CH3:3])[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 12345442HCID 12345442, compound

Product 1

HCID 10749418HCID 10749418, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid NaBH4 (0.19 g, 5.03 mmol) was added portionwise to a stirred solution of 1-methyl-5-nitro-2-pyrrolealdehyde (42) [for preparation see Fournari, P. Bull. Soc. Chim. Fr., 88, 488-491, 1963] (0.78 g, 5.07 mmol) in MeOH (40 mL) at room temperature under N2. After addition was complete, the reaction mixture was stirred for a further 20 min, then water (40 mL) was added and the mixture was saturated with solid K2CO3. Extraction with EtOAc gave 2-hydroxymethyl-1-methyl-5-nitropyrrole (43) (0.77 g, 97%), mp (EtOAc/petroleum ether) 76-77° C. 1H NMR (CDCl3) δ 7.16 (d, J=4.3 Hz, 1 H, H-4), 6.17 (d, J=4.3 Hz, 1 H, H-3), 4.68 (s, 2 H, CH2), 4.02 (s, 3 H, CH3). Anal. Calculated for C6H8N2O3 : C, 45.1; H, 5.2; N, 17.9. Found: C, 46.1; H, 5.1; N, 17.6%.

Workup

  1. additionAfter addition
  2. extractionExtraction with EtOAc

Sources & evidence

ORD record
ord-4a4116065db84d0996466e36c9b9a89b
Source dataset
uspto-grants-2000_06
Patent number
US06071908

Reaction notes

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