Water → HCID 20109578, compound

HRID 2406565Notes

Reaction equation

HRID 2406565 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:10].[CH3:18][O:19][CH2:20]Br.O>CN(C)C=O>[CH3:18][O:19][CH2:20][CH2:1][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[CH2:8][CH3:7])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62714'-HydroxypropiophenoneHCID 10796Cesium carbonateHCID 83093Bromomethyl methyl ether

Product 1

HCID 20109578HCID 20109578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (5.7 g, 17.5 mmol) was added to a stirred solution of 4-hydroxypropiophenone (12; 2.5 g, 16.7 mmol) in dimethylformamide (25 mL) under nitrogen at room temperature, followed by bromomethyl methyl ether (1.43 g, 17.5 mmol). After 20 hours the mixture was stirred into 200 mL of water, and then extracted 3× with dichloromethane. The combined extracts were washed with water and then sat brine, and dried over magnesium sulfate. The solvent was removed in vacuo, leaving 3.4 g of pale yellow apparently crystalline solid; mp 31-35° C.; mass spec ES+m/z=209 (m+1).

Workup

  1. extractionextracted 3× with dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customleaving 3.4 g of pale yellow apparently crystalline solid

Sources & evidence

ORD record
ord-4b87e5929b8240ffa0674357b6158b7f
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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