Ethyl Acetate → HCID 19382486, compound

HRID 2400194Notes

Reaction equation

HRID 2400194 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11]Br)=[C:6]([CH2:15][CH2:16][CH3:17])[C:5]=1[OH:18])(=[O:3])[CH3:2].[OH:19][CH:20]([C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>C(#N)C>[OH:18][C:5]1[C:6]([CH2:15][CH2:16][CH3:17])=[C:7]([O:8][CH2:9][CH2:10][CH2:11][O:36][C:33]2[CH:32]=[CH:31][C:30]([CH:20]([OH:19])[CH2:21][CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:35][CH:34]=2)[CH:13]=[CH:14][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 19382483HCID 19382483, compound

Product 1

HCID 19382486HCID 19382486, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl bromide (J. Med. Chem. 29, 1573-1576, 1986) (315 mg) and the phenol of Step 1 (242 mg) in acetonitrile (5 mL) was added cesium carbonate (650 mg) and the mixture was heated to reflux for 5 hrs. The suspension was cooled to 25° C. and poured into 25% aqueous NH4OAc and EtOAc. The organic layer was washed with brine, dried with MgSO4 and the solvents are removed in vacuo. The residue was purified by chromatography on silica gel using EtOAc and hexanes (1:2) to yield the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hrs
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. customthe solvents are removed in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-28d0e72f7b6e4afea01f575be1e0f472
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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