Methyl iodide → HCID 66874894, compound

HRID 516847Notes

Reaction equation

HRID 516847 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1.[Li+].[CH3:24][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:24])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 66875723Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate

Product 1

HCID 66874894HCID 66874894, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)phenyl)acetate (Step B, 4 g, 13.6 mmol) in dry THF (30 ml) at −68° C. under a dry argon atmosphere was added LiHMDS drop wise (1 M solution in THF, 17.45 ml, 17.4 mmol), and the resulting orange solution was stirred at low temperature for 30 minutes before CH3I (5.71 g, 40.26 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for another 15 hours. The reaction was quenched with ice, and the product was extracted with EtOAc (2×), the organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ether, 5:1) to give the title compound.

Workup

  1. additionwas added
  2. customThe reaction was quenched with ice
  3. extractionthe product was extracted with EtOAc (2×)
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex:ether, 5:1)

Sources & evidence

ORD record
ord-6b90fef99a52412babdd04af7c5b3851
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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