Cesium carbonate → Methyl 4-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-3-chlorophenylacetate

HRID 2185033Notes

Reaction equation

HRID 2185033 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17]Br)=[C:10]([CH2:19][CH2:20][CH3:21])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:26]=[CH:27][C:28]=1[OH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:19]([C:10]1[CH:9]=[C:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH2:15][CH2:16][CH2:17][O:29][C:28]1[CH:27]=[CH:26][C:25]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=1[Cl:22])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 92625Methyl 3-chloro-4-hydroxyphenylacetateHCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

Product 1

HCID 22458934Methyl 4-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-3-chlorophenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Step A (2.5 g, 7.18 mmol), methyl 3-chloro-4-hyrdoxyphenylacetate (1.42 g, 7.11 mmol) and cesium carbonate (2.43 g, 7.45 mmol) in DMF (20 mL) was stirred at 40° C. overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic was washed twice with water, then dried over sodium sulfate. The organic was filtered and evaporated to an oil which was chromatographed over silica gel with 10% of ethyl acetate in hexane to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.2N HCl
  2. washThe organic was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic was filtered
  5. customevaporated to an oil which
  6. customwas chromatographed over silica gel with 10% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-11d53e0bb3114b36ac840aaef3f04375
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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