Diazomethane → HCID 57364289, compound

HRID 705016Notes

Reaction equation

HRID 705016 reaction equation
[N+:1](=[CH2:3])=[N-:2].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9](Cl)=[O:10]>CCOCC>[N+:1](=[CH:3][C:9]([C:5]1[O:4][CH:8]=[CH:7][CH:6]=1)=[O:10])=[N-:2]

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 682422-Furancarbonyl chloride

Product 1

HCID 57364289HCID 57364289, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

N-Nitroso-N-methylurea (16.14 g, 61.53 mmol) was treated with a concentrated NaOH aqueous solution to produce diazomethane. The diazomethane was combined with dry ether (100 ml), dried over KOH, and the resulting ethereal solution was cooled in an ice-salt bath. A solution of furan-2-carbonyl chloride (1.6 g, 12.3 mmol) in dry ether (25 ml) was then added very slowly to the diazomethane solution. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated to dryness (under an argon atmosphere, and keeping the water bath temperature below 25° C.), and the resulting crude material was purified by column chromatography using 230-400 mesh silica gel and 1% triethylamine in DCM solvent system. Evaporation of solvent yielded 2-diazo-1-(furan-2-yl)ethanone as a yellow oil (900 mg, 49%).

Workup

  1. dry with materialdried over KOH
  2. temperaturethe resulting ethereal solution was cooled in an ice-salt bath
  3. customThe solvent was evaporated to dryness (under an argon atmosphere
  4. customthe water bath temperature below 25° C.
  5. customwas purified by column chromatography
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-bac9df116c9947de88bc7d2030054c47
Source dataset
uspto-grants-2015_11
Patent number
US09173401B2

Reaction notes

Loading…