Ethanol → HCID 10956036, compound

HRID 1748901Notes

Reaction equation

HRID 1748901 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-27c9301cd4c842f892efc4044b60a657
Source dataset
uspto-grants-2015_10
Patent number
US09151739B2

Reaction notes

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