Sodium Iodide → HCID 67530671, compound

HRID 499024Notes

Reaction equation

HRID 499024 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[O:9][CH2:8][CH2:7][C:6]2(O[Si](C)(C)C)[C:14]#[N:15].C[Si](Cl)(C)C.[I-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]#[N:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 67530367HCID 67530367, compound

Product 1

HCID 67530671HCID 67530671, 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 0.9 gram (0.0046 mole) of 6-methoxy-7-methylchroman-4-one (ii) with 1.40 grams (0.0138 mole) of trimethylsilyl cyanide, in the presence of 0.1 gram (catalyst) of aluminum chloride in 30 mL of toluene, affording an intermediate product, namely: 6-methoxy-7-methyl-4-(1,1-dimethyl-1-silaethoxy)chromane-4-carbonitrile (cyano-silyl intermediate), then 2) the reaction of the 1-silaethoxy intermediate with 2.35 mL (0.0184 mole) of trimethylsilyl chloride, 2.8 grams (0.0184 mole) of sodium iodide, and 0.12 mL of water in 30 mL of acetonitirile, yielding 0.6 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-aa3a984f5e2b4e8e8440686a9c07c263
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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