Methyl iodide → 1,2-Diphenylpropan-1-one

HRID 1371037Notes

Reaction equation

HRID 1371037 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16]C(C)([O-])C.[K+].CI>C1COCC1>[C:1]1([C:7](=[O:8])[CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 99482-PhenylacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 2385181,2-Diphenylpropan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To deoxybenzoin (0.500 g, 2.55 mmol) in THF (12 mL) at −78° C. were added a THF solution of potassium tert-butoxide 1M (2.5 mL, 2.55 mmol) and MeI (0.396 mL). After a period of 0.5 h, at room temperature, NH4OAc aqueous was added to the reaction mixture. The organic phase was separated, dried over NaSO4, filtered and evaporated. The residue was purified by flash chromatography to give the title compound.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over NaSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9da52f0a7cef4fd0a94c0f3cb266a115
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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