Iodoethane → HCID 58136776, compound

HRID 532371Notes

Reaction equation

HRID 532371 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([OH:14])[C:10]=1[O:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[CH2:18](I)[CH3:19].[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([O:14][CH2:18][CH3:19])[C:10]=1[O:11][CH2:12][CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58136834HCID 58136834, compound

Product 1

HCID 58136776HCID 58136776, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(3-tert-Butyl-4-ethoxy-5-hydroxyphenyl)ethanone (O3.010; 470 mg) and ethyl iodide (193 μl) were dissolved in DMF (6.2 ml), and sodium hydride (57 mg) was added. After stirring at RT for 0.5 h, the DMF was drawn off and the residue was taken up in EA, washed with water, dried and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient 0-30% within 60 min). 420 mg of the title compound were obtained. LC MS rt: 1.93 min [M+H]+: 265.2 (met. a)

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified
  5. customsilica gel (40 g cartridge, n-heptane/EA gradient 0-30% within 60 min)

Sources & evidence

ORD record
ord-cc9256ba8e9e49a5b4d755e3d16897e1
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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