Sodium Iodide → HCID 67530272, compound

HRID 499018Notes

Reaction equation

HRID 499018 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-435497785e6149a89613c1c8a3d4e09e
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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