Sodium Iodide → HCID 53945126, compound

HRID 1859800Notes

Reaction equation

HRID 1859800 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(C#N)(C)=O.[Na+].[I-].Cl[Si:21]([CH3:24])([CH3:23])[CH3:22]>>[CH3:22][Si:21]([CH3:24])([CH3:23])[O:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH:7]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 694302-OxopropiononitrileHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 53945126HCID 53945126, compoundYield 83.2%

Procedure

To a solution of 6-hydroxytetralone (0.972 g, 6.0 mmol) in 10 mL of freshly distilled AcCN at room temperature was added sequentially dry NaI (2.25 g, 15 mmol), TEA (2.10 mL, 15 mmol), and chlorotrimethylsilane (1.92 mL, 15 mmol). After stirring for 1 hour, the reaction was quenched with the addition of a cold solution of saturated ammonium chloride and the reaction was extracted into Et2O (2×100 mL). The combined extracts were washed with ice cold water and then dried, filtered, and concentrated in vacuo to afford 1.53 g of the title compound as a colorless oil which was used for further reaction without purification.

Workup

  1. customthe reaction was quenched with the addition of a cold solution of saturated ammonium chloride
  2. extractionthe reaction was extracted into Et2O (2×100 mL)
  3. washThe combined extracts were washed with ice cold water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92a91c550b774adeb50316326e21304a
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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