Iodoethane → HCID 66875058, compound

HRID 1925232Notes

Reaction equation

HRID 1925232 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][CH:25]([N-]C(C)C)C.CCI>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[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]([CH2:24][CH3:25])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 66875723Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate

Product 1

HCID 66875058HCID 66875058, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred solution of Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate (Step B, 4.84 g, 16.2 mmol) in dry THF (60 ml) and HMPA (15 ml) at −78° C. under a dry argon atmosphere was added LDA drop wise (2 M solution in THF, 25 ml, 48.72 mmol), and the resulting orange solution was stirred at low temperature for 30 minutes before CH3CH2I (10.13 g, 64.96 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for 15 hours. The reaction was quenched with aqueous citric acid, and the product was extracted with EtOAc (2×), the organic phase washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-6680f59a55164a17a7fa2da6c9a1a30f
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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