Sodium Chloride → HCID 20144429, compound

HRID 649040Notes

Reaction equation

HRID 649040 reaction equation
[C:1]([C:3]1[C:7]([C:8](OC)=[O:9])=[CH:6][N:5]([CH2:12][C:13]#[CH:14])[CH:4]=1)#[N:2].O1CCCC1.[BH4-].[Li+].[Cl-].[Na+]>O>[OH:9][CH2:8][C:7]1[C:3]([C:1]#[N:2])=[CH:4][N:5]([CH2:12][C:13]#[CH:14])[CH:6]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21278482HCID 21278482, compound

Product 1

HCID 20144429HCID 20144429, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

3.90 g of methyl 3-cyano-1-(2-propynyl)-1H-pyrrole-4-carboxylate, 35 ml of tetrahydrofuran, 11 ml of water and 1.556 g of lithium borohydride were mixed together and stirred for 3 hours 30 minutes at 20° C. The reaction mixture was poured into a saturated aqueous solution of sodium chloride with stirring and was extracted with ethyl acetate. The extracts were concentrated to dryness by distilling under reduced pressure and the residue was chromatographed over silica. Elution with a mixture of hexane and ethyl acetate (4-6) yielded 1.33 g of 4-hydroxymethyl-1-(2-propynyl)-1H-pyrrole-3-carbonitrile melting at 95° C.

Workup

  1. stirringwith stirring
  2. extractionwas extracted with ethyl acetate
  3. concentrationThe extracts were concentrated to dryness
  4. distillationby distilling under reduced pressure
  5. customthe residue was chromatographed over silica
  6. washElution
  7. additionwith a mixture of hexane and ethyl acetate (4-6)

Sources & evidence

ORD record
ord-987f9634788f48e2b69d6f364973d957
Source dataset
uspto-grants-1988_04
Patent number
US04737513

Reaction notes

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