Diazomethane → HCID 54486441, compound

HRID 971843Notes

Reaction equation

HRID 971843 reaction equation
[CH:1]1([CH2:7][C:8](Cl)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:11](=[CH2:13])=[N-:12]>CCOCC>[N+:11](=[CH:13][C:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:9])=[N-:12]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 2757989Cyclohexylacetyl chloride

Product 1

HCID 54486441HCID 54486441, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 19.8 g of cyclohexylacetyl chloride (b.p. 98°-100°/23 mm Hg) in 150 ml of dry ether is slowly added at 0°-5° with cooling in an ice-water bath to a vigorously stirred solution of 11 g of diazomethane in 500 ml of ether. The excess diazomethane and ether is distilled off under reduced pressure and cyclohexylmethyl diazomethyl ketone is obtained as residue; infra-red absorption spectrum (in methylene chloride): characteristic bands at 3.45μ, 3.52μ, 4.75μ and 6.12μ; the product is processed without any further purification. A solution of 20 g of cyclohexalmethyl diazomethyl ketone in 100 ml of ether is added in one portion, with stirring, to a solution of 32 g of triphenylphosphine in 450 ml of ether. After stirring for 30 minutes at room temperature, the solvent is evaporated under reduced pressure. The 1-cyclohexyl-3-(triphenylphosphoranylidene-hydrazono)-acetone obtainable as oily residue crystallises in the cold from ether; m.p. 58°-62°; ultra-violet absorption spectrum: λmax 314 mμ, 262-275 mμ and 223 mμ (in ethanol and in potassium hydroxide/ethanol), and λmax 257-275 mμ and 230 mμ (in hydrogen chloride/ethanol); infra-red absorption spectrum (in methylene chloride): characteristic bands at 3.43μ, 3.56μ, 4.76μ, 6.15μ and 6.67μ.

Workup

  1. distillationThe excess diazomethane and ether is distilled off under reduced pressure

Sources & evidence

ORD record
ord-ced3093a1e8f445dab76660048b880ad
Source dataset
uspto-grants-1979_07
Patent number
US04161476

Reaction notes

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