{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid ethyl ester → {4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid

HRID 751489Notes

Reaction equation

HRID 751489 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:14]2[O:13][CH:12]=[CH:11][C:10]=2[C:9]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:8][CH:7]=1)C>CN(C)C=O.C(OCC)(=O)C>[O:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[O:18][CH2:17][CH2:16][O:15][C:9]1[C:10]2[CH:11]=[CH:12][O:13][C:14]=2[C:6]([CH2:5][C:4]([OH:25])=[O:3])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 69268314{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid ethyl ester

Product 1

HCID 69270245{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add to a cooled solution (0° C.) of {4-[2-(tetrahydropyran-2-yloxy)ethoxy]-benzofur-7-yl}acetic acid ethyl ester (1.363 g, 3.912 mmol) in dimethylformamide (20 ml) 2M aqueous sodium hydroxide (10 ml), and stir the mixture for 1½ hours at room temperature. Dilute the mixture with ethyl acetate and extract with water. Dilute with methylene chloride (50 ml) and neutralize using 0.1M aqueous hydrochloric acid (100 ml). Separate the layers are separated and extract the water layer with methylene chloride. Combine the methylene chloride layers, dry over sodium sulfate, filter, and concentrate to obtain 0.920 g (68%) of the title compound as an oil. Mass spectrum: electrospray (m/z) 319 (M−1).

Workup

  1. extractionextract with water
  2. additionDilute with methylene chloride (50 ml)
  3. customSeparate the layers
  4. customare separated
  5. extractionextract the water layer with methylene chloride
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-2fb0db823da44c1b8d3b3218109c4e65
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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