Methyl iodide → HCID 67958584, compound

HRID 527642Notes

Reaction equation

HRID 527642 reaction equation
Br[C:2]1[C:10]2[O:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=2[C:5]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[CH3:24]N(C)CCN(C)C.C([Li])CCC.CCCCCC.CI>C1COCC1>[CH3:16][CH:15]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[O:13][C:5]1[C:6]2[C:7]([CH3:12])([CH3:11])[CH2:8][O:9][C:10]=2[C:2]([CH3:24])=[CH:3][CH:4]=1)[CH3:17]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 67958735HCID 67958735, compound2×HCID 178418339Butyllithium

Product 1

HCID 67958584HCID 67958584, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[(7-bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy][tris(1-methylethyl)]silane (Intermediate 182, 7.1 g, 17.72 mmol) was dissolved in anhydrous THF (72 mL) and cooled to 0° C. Tetramethylethylenediamine (8.0 mL, 53.16 mmol) was added and the yellow solution was stirred at 0° C. for 10 min. A solution of 1.6 M butyllithium in hexane (22.5 mL, 35.4 mmol) was added drop wise over 10 minutes and then stirred at 0° C. for 15 min. Methyl iodide (11 mL, 177.2 mmol) was added drop wise over 6 min. The white solid was removed by filtration and the wet cake was washed in with THF. The combined organic layers were evaporated to dryness. The residue was dissolved in ethyl acetate and washed twice with aqueous NaHCO3 and once with water. The organic solution was dried on anhydrous Na2SO4 and evaporated to dryness. to give brown oil. The residue was purified by flash chromatography on silica gel using cyclohexane to cyclohexane/ethyl acetate 1:1 as eluents affording the title compound (3.6 g) as a brown oil.

Workup

  1. stirringstirred at 0° C. for 15 min
  2. customThe white solid was removed by filtration
  3. washthe wet cake was washed in with THF
  4. customThe combined organic layers were evaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed twice with aqueous NaHCO3 and once with water
  7. dry with materialThe organic solution was dried on anhydrous Na2SO4
  8. customevaporated to dryness
  9. customto give brown oil
  10. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1dd87d5f50784bfd80108c08aa4cb3b6
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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