Sulfuric Acid → HCID 12383845, compound

HRID 1184865Notes

Reaction equation

HRID 1184865 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8]C(OCC)=O)=[O:7].[OH-].[K+].[N:16]([O-])=[O:17].[Na+].S(=O)(=O)(O)O>O.CCOCC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:7])/[CH:8]=[N:16]/[OH:17]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoateHCID 23668193Sodium Nitrite

Product 1

HCID 12383845HCID 12383845, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-(fur-2-oyl)acetate (5.38 g, 29.5 mmol) and potassium hydroxide (2.70 mL, 2.7 g, 48.1 mmol) in water (70 mL) was stirred overnight at rt. sodium nitrite (2.038 g, 29.5 mmol) in water (10 mL) was added and cooled down to 0° C. A solution of 6N sulfuric acid in water (14 mL) was added drop wise and stirred for 15 min (precipitate was formed). Ether was added and the water layer was extracted twice with ether. The combined organic layers were washed with water, dried and evaporated. Crystallization with CH2Cl2 gave (E)-2-(furan-2-yl)-2-oxoacetaldehyde oxime 54 (2.52 g, 61.3%). NMR (400 MHz, CDCl3) 6.59 (q, J=3.5 and 1.5 Hz, 1H), 7.55 (dd, J=3.5 and 0.8 Hz, 1H), 7.72 (m, 1H), 7.96 (s, 1H), 8.27 (br s, 1H).

Workup

  1. custom(precipitate was formed)
  2. extractionthe water layer was extracted twice with ether
  3. washThe combined organic layers were washed with water
  4. customdried
  5. customevaporated
  6. customCrystallization with CH2Cl2

Sources & evidence

ORD record
ord-f461e75878da47f1854c9353e9198bf4
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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