4'-Hydroxyacetophenone → HCID 22031502, compound

HRID 1792446Notes

Reaction equation

HRID 1792446 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl>ClCCl>[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 22031502HCID 22031502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While 30 mL solution of 2.72 g 4-hydroxyacetophenone and 5.2 mL diisopropyl ethylamine in dichloromethane was stirred under ice-cooling in a stream of nitrogen, 4.2 mL 2-(trimethylsilyl)ethoxymethyl chloride was added thereto. Then, the reaction solution was stirred at room temperature for 4 hours. The reaction solution was evaporated, then ethyl acetate and water were added to the residue, the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 5.22 g of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. customThe reaction solution was evaporated
  3. additionethyl acetate and water were added to the residue
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d4c5a74becb748159582e59b4d9a4a5e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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