Ethanol → HCID 66724991, compound

HRID 1616975Notes

Reaction equation

HRID 1616975 reaction equation
[N+](=[CH:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[N-].Cl[O:16][C:17]([CH3:20])(C)C.[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][CH:3]([O:16][CH2:17][CH3:20])[C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 521297Tert-Butyl hypochloriteHCID 713384101-Diazonio-3-(3-methoxyphenyl)prop-1-en-2-olate

Product 1

HCID 66724991HCID 66724991, compound

Procedure

Under an argon atmosphere, 1-diazo-3-(3-methoxyphenyl)propan-2-one (82) (501 mg, 2.63 mmol) was dissolved in anhydrous ethanol (5 mL) and cooled to −18C. To this was added tert-butyl hypochlorite (300 μL, 2.65 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═10/1) to give 1,1-diethoxy-3-(3-methoxyphenyl)propan-2-one (83) as a pale yellow oily substance (371 mg, 1.47 mmol, 55.8%).

Workup

  1. temperaturecooled to −18C
  2. concentrationAfter concentrating under reduced pressure
  3. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate═10/1)

Sources & evidence

ORD record
ord-17b993c730704a2ba7099c9e4f0affeb
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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