Ethanol → HCID 10956036, compound

HRID 1616972Notes

Reaction equation

HRID 1616972 reaction equation
[N+](=[CH:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][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][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 521297Tert-Butyl hypochloriteHCID 54230507HCID 54230507, compound

Product 1

HCID 10956036HCID 10956036, compound

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1-diazo-3-(4-methoxyphenyl)propan-2-one (62) (477 mg, 2.51 mmol) was dissolved in anhydrous ethanol (5 mL) and cooled to 0° C. To this was added tert-butyl hypochloride (285 μL, 2.52 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-(4-methoxyphenyl)propan-2-one (63) as a colorless oily substance (357 mg, 1.41 mmol, 56.4%).

Workup

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

Sources & evidence

ORD record
ord-d6475edc42804288bf865d2283de8764
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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