1,4-Dioxane → HCID 67324768, compound

HRID 1616931Notes

Reaction equation

HRID 1616931 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].O1CCOCC1.[H-].[Li+].Br[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[CH:22]=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:27][C:25]1[CH:26]=[C:21]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:22]=[C:23]([O:29][CH3:30])[CH:24]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62714Lithium hydrideHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 3435097Tris(propan-2-yl)silanethiol

Product 1

HCID 67324768HCID 67324768, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of triisopropylsilanethiol (0.49 g, 2.6 mmol) in 1,4-dioxane (5 mL, 60 mmol) was added lithium hydride (23 mg, 2.9 mmol). After 10 minutes, 1-bromo-3,5-dimethoxy-benzene (500 mg, 2 mmol) and tetrakis(triphenylphosphine)palladium(0) (270 mg, 0.23 mmol) were added and the reaction mixture was heated to 60° C. for 16 h. The reaction mixture was diluted with DCM, filtered and concentrated. The resulting residue was dissolved in DCM and purified using silica gel chromatographie (40 g silica gel column) eluting with hexanes:DCM (3:1) to afford the title product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in DCM
  4. custompurified
  5. washeluting with hexanes:DCM (3:1)

Sources & evidence

ORD record
ord-87878244df3f483ba04bced7870a61e9
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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