Sodium Iodide → HCID 67530272, compound

HRID 2220175Notes

Reaction equation

HRID 2220175 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O[Si](C)(C)C)([C:12]#[N:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.C[Si](Cl)(C)C.[I-].[Na+]>O>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:12]#[N:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 67530784HCID 67530784, compound

Product 1

HCID 67530272HCID 67530272, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared in a manner analogous to that of Step E of Example 2, by 1) the reaction of 1.0 gram (0.006 mole) of 7-methylchroman-4-one (ii) with 1.8 gram (0.018 mole) of trimethylsilyl cyanide, in the presence of 0.2 gram (catalyst) of aluminum chloride in 30 mL of toluene, affording an intermediate product, namely: 7-methyl-4-(1,1-dimethyl-1-silaethoxy)chromane-4-carbonitrile (cyano-silyl intermediate), then 2) the reaction of the 1-silaethoxy intermediate with 3 mL (0.024 mole) of trimethylsilyl chloride, 3.6 grams (0.024 mole) of sodium iodide, and 0.2 mL of water in 30 mL of acetonitirile, yielding 0.8 gram of subject compound. Contrary to Step E of Example 2, the hydrogenation step was not necessary to obtain the subject compound. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-4b37dc3ba7584cb8bc35d436beef0d82
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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