Tetrahydrofuran → HCID 66760852, compound

HRID 561868Notes

Reaction equation

HRID 561868 reaction equation
C1COCC1.[C:6](/[C:8](=[CH:13]\[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]2[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=2[Cl:32])=[CH:16][CH:15]=1)/[C:9]([O:11]C)=[O:10])#[N:7].[OH-].[Na+]>CO>[C:6](/[C:8](=[CH:13]\[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]2[C:25]([Cl:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=2[Cl:30])=[CH:18][CH:19]=1)/[C:9]([OH:11])=[O:10])#[N:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66761590HCID 66761590, compound

Product 1

HCID 66760852HCID 66760852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2:1 (v/v) THF:MeOH solution (0.1 M) of methyl (2E)-2-cyano-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}acrylate from Example 9, Step 1 (1 eq.) was added sodium hydroxide (1.0 M aq. solution, 3 eq.). The resulting solution was stirred at RT for 18 h before the volatiles were removed in vacuo. Following careful acidification of the resulting mixture to pH ˜1 with 10% aq. HCl, the solution was extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a yellow semi-solid.

Workup

  1. customwere removed in vacuo
  2. extractionthe solution was extracted with EtOAc
  3. washThe combined organic extracts were washed further with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bf40dc669d9442f8a84cc3ac8d7f6247
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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