Ethanol → HCID 66724991, compound

HRID 1748904Notes

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

Reactant 3

HCID 702Ethanol

HCID 521297Tert-Butyl hypochlorite

HCID 713384101-Diazonio-3-(3-methoxyphenyl)prop-1-en-2-olate

Product 1

HCID 66724991HCID 66724991, compound

Conditions

Temperature: -18 °C

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 −18° C. 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

concentrationAfter concentrating under reduced pressure
customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-8638d6ade1b848a8bac56225367cb3c3
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09151739B2

Reaction notes

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