Acetic Acid → HCID 66920530, compound

HRID 1880341Notes

Reaction equation

HRID 1880341 reaction equation
C(O)(=O)C.Cl.[O:6]1[CH2:10][CH2:9][CH:8]([NH:11][NH2:12])[CH2:7]1.[CH:13](=O)[C:14]([CH3:16])=[O:15].[Na+].[Cl-]>O>[O:6]1[CH2:10][CH2:9][CH:8]([NH:11][N:12]=[CH:13][C:14](=[O:15])[CH3:16])[CH2:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 880MethylglyoxalHCID 5234Sodium ChlorideHCID 19432761(Tetrahydrofuran-3-yl)hydrazine hydrochloride

Product 1

HCID 66920530HCID 66920530, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetic acid (1.7 mL) was slowly added to a solution of tetrahydrofuran-3-ylhydrazine hydrochloride (2.50 g, 18.0 mmol) (prepared as described by Bacon, E. R.; Singh, B.; and Lesher, G. Y. in U.S. Pat. No. 5,294,612) in water (30 mL). This mixture was then added dropwise to a solution of pyruvaldehyde (2.59 g, 2.34 mL, 14.4 mmol) in water (240 mL). The mixture was stirred overnight at room temperature. The mixture was poured into a seperatory funnel, NaCl was added and dissolved in the aqueous phase and then extracted with CH2Cl2 (6-times). The combined organic extracts were dried over Na2SO4, filtered and concentrated to provide crude material, which was purified by preadsorbing the oil on SiO2 followed by chromatography (Isco, 80 g RediSep column) eluting with a 0-80% EtOAc/heptane gradient over 80 minutes. Analysis of fractions resulted in isolation of 2-oxopropanal tetrahydrofuran-3-ylhydrazone (1.19 g, 53%).

Workup

  1. customprepared
  2. additionThe mixture was poured into a seperatory funnel
  3. dissolutiondissolved in the aqueous phase
  4. extractionextracted with CH2Cl2 (6-times)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide crude material, which
  9. customwas purified
  10. washeluting with a 0-80% EtOAc/heptane gradient over 80 minutes

Sources & evidence

ORD record
ord-c0b42638945343b8864f0e1d528c697f
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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