Methyl iodide → HCID 67519647, compound

HRID 1925236Notes

Reaction equation

HRID 1925236 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][CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][CH:11]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CI.[CH2:35]1COC[CH2:36]1>>[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][CH:13]([CH3:17])[C:14]([O:16][CH2:35][CH3:36])=[O:15])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 16662683HCID 16662683, compound

Product 1

HCID 67519647HCID 67519647, compound

Procedure

To a stirred solution of Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate (Step B, 4.53 g, 14.5 mmol) in dry THF (30 ml) at −68° C. under a dry argon atmosphere was added LiHMDS drop wise (1 M solution in THF, 21.77 ml, 21.77 mmol), and the resulting orange solution was stirred at low temperature for 30 minutes before CH3I (20.60 g, 145.2 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for 15 hours. The reaction was quenched with ice, and the product was extracted with EtOAc (2×), the organic phase 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 phase 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-4ef0cf046dc84202905045efaf098115
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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