Ethanol → HCID 71236733, compound

HRID 920309Notes

Reaction equation

HRID 920309 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1.S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH2:31](O)[CH3:32]>>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:31][CH3:32])=[O:14])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 71236792HCID 71236792, compound

Product 1

HCID 71236733HCID 71236733, compoundYield 78%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(6-(3,4-difluorophenoxy)pyridin-3-yl)acetic acid (10 g, 37.7 mmol) in ethanol (100 mL) was added sulfuric acid (20 ml, 375 mmol) in ethanol (100 mL). The reaction mixture was stirred at 80° C. for 3 hr. and then the reaction mixture was made alkali with Na2CO3, and then extracted with CH2Cl2. The organic layer was separated and dried over Na2SO4, and then concentrated under reduced pressure to provide ethyl 2-(6-(3,4-difluorophenoxy)pyridin-3-yl)acetate (10 g, 78%).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0b896bb25f8491e9477d5fc6170afc4
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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