Diethyl Ether → HCID 3296813, compound

HRID 893225Notes

Reaction equation

HRID 893225 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C1C2C(=CC=CC=2)C=CC=1S([N:25]=[N+:26]=[N-])(=O)=O.C(N(CC)CC)C.C(OCC)C>C(#N)C>[N+:25](=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[N-:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7761Diethyl MalonateHCID 8471TriethylamineHCID 109773552-Naphthalenesulfonyl azide

Product 1

HCID 3296813HCID 3296813, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 24.52 grams (0.15 mole) of diethyl malonate and 34.0 grams (0.15 mole) of 2-naphthalenesulfonyl azide in 100 milliliters of acetonitrile was added 15.49 grams (0.15 mole) of triethylamine, dropwise, with cooling at 0° C.-5° C. On completing the feed the mixture was allowed to warm to room temperature while stirring for an approximate 16-hour period. Volatiles were stripped from the mixture under reduced pressure and the residue was slurried with ethyl ether and the inorganic salt filtered off. The filtrate was evaporated free of ether and purified by silica column chromatography to give 27.03 grams (0.15 mole) of diethyl diazomalonate as a yellow liquid. NMR analysis of the product indicated the following:

Workup

  1. temperaturedropwise, with cooling at 0° C.-5° C
  2. filtrationthe inorganic salt filtered off
  3. customThe filtrate was evaporated free of ether
  4. custompurified by silica column chromatography

Sources & evidence

ORD record
ord-b0e5ffdac5fe4f1e80b5f960018f61a6
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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