HCID 19041763, compound → HCID 19041803, compound

HRID 1684050Notes

Reaction equation

HRID 1684050 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[O:17][CH2:16][CH2:15]C[O:13]2)[CH:6]=[C:7](I)[C:8]=1[O:9][CH3:10].[Cu](C#N)[C:19]#[N:20]>CN(C=O)C>[C:19]([C:7]1[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH:12]2[O:13][CH2:15][CH2:16][O:17]2)[CH:6]=1)#[N:20]

Participants

4

Reactant 2

HCID 19041763HCID 19041763, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 19041803HCID 19041803, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3,4-dimethoxy-5-iodophenyl)-1,3-dioxolane (42) (FIG. 22) (2.80 g, 8.0 mmole), copper cyanide (5.7 g, 32.0 mmole) and dry DMF (50 ml) were stirred under an argon atmosphere for 24 hours at 140° C. The reaction was cooled to room temperature, filtered through celite, and the filtrate concentrated to an oil in vacuo. The dark brown oil was purified through a short flash silica column using 2:1 hexane/ethyl acetate as eluent to yield 1.471 g (74%) of a white solid. The product can be recrystallized from hexane/ethyl acetate.

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate concentrated to an oil in vacuo
  3. customThe dark brown oil was purified through a short flash silica column

Sources & evidence

ORD record
ord-9186480dfa084ecebfb29ab10aeeb4e9
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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