Ethanol → HCID 66724985, compound

HRID 1037585Notes

Reaction equation

HRID 1037585 reaction equation
[N+](=[CH:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)=[N-].Cl[O:15][C:16]([CH3:19])(C)C.[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][CH:3]([O:15][CH2:16][CH3:19])[C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 521297Tert-Butyl hypochloriteHCID 76661290HCID 76661290, compound

Product 1

HCID 66724985HCID 66724985, compound

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1-diazo-3-(4-iodophenyl)propan-2-one (13) (1.11 g, 3.88 mmol) was dissolved in anhydrous ethanol (10 mL) and cooled to 0° C. To this was added tert-butyl hypochlorite (440 μL, 3.89 mmol) and stirred for an hour at the same temperature. After concentrating under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=9/1) to give 1,1-diethoxy-3-(4-iodophenyl)propan-2-one (14) as a yellow oily substance (758 mg, 2.18 mmol, 56.1%).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-95292d3d3dea445ebd07cff6bdfefe7a
Source dataset
uspto-grants-2013_10
Patent number
US08546568B2

Reaction notes

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