Chlorotrimethylsilane → HCID 15480784, compound

HRID 842944Notes

Reaction equation

HRID 842944 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([CH:13]=O)=[CH:5][CH:4]=1.[Br-:15].[Li+].C[Si](Cl)(C)C.C[SiH](C)O[SiH](C)C>C(#N)C.ClCCl.CN(C=O)C>[Br:15][CH2:13][C:6]1[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 82050Lithium BromideHCID 4359894HCID 4359894, compound

Product 1

HCID 15480784HCID 15480784, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-methoxy-1,4-benzodioxane-5-carbaldehyde (12 g, 62 mmol) in acetonitrile (140 mL) was added lithium bromide (12 g, 110 mmol), and then trimethylsilyl chloride (12 mL, 95 mmol) was added dropwise. After 15 minutes, the mixture was ice-cooled, and 1,1,3,3-tetramethyldisiloxane (19 mL, 110 mmol) was added dropwise, followed by stirring at room temperature for 2 hours. The mixture was diluted with dichloromethane, and then was filtered through Celite. The solvent was evaporated in vacuo to give a pale yellow oil. To a solution of the obtained crude 5-bromomethyl-8-methoxy-1,4-benzodioxane in DMF(180 mL) was added sodium cyanide (9.2 g, 190 mmol), followed by stirring at room temperature for 60 hours. To the mixture was added water under ice-cooling, and the precipitated solid was collected by filtration to give Compound 1a (6.8 g, 53%) as an ash-colored solid.

Workup

  1. temperaturecooled
  2. filtrationwas filtered through Celite
  3. customThe solvent was evaporated in vacuo
  4. customto give a pale yellow oil

Sources & evidence

ORD record
ord-c762ceb6bce944419c3414e4edaec73a
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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