Sodium Hydroxide → HCID 10177222, compound

HRID 896485Notes

Reaction equation

HRID 896485 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:27]=[CH:26][C:13]([CH2:14][CH:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18]CC)=[O:17])=[CH:12][CH:11]=2)[C:5]2[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=2[O:3]1.[OH-].[Na+]>O1CCCC1>[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:14][CH:15]([C:16]([OH:18])=[O:17])[C:21]([OH:23])=[O:22])=[CH:26][CH:27]=2)[C:5]2[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10159558Diethyl 2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}malonate

Product 1

HCID 10177222HCID 10177222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the compound obtained in Example 2 (1.5 g) in tetrahydrofuran (20 ml). Add 2N sodium hydroxide (8 ml) to the reaction mixture, cooled to 0° C. using an ice bath. Stir magnetically at ambient temperature for 72 hours. Remove the tetrahydrofuran by evaporation under reduced pressure. Take up the resulting residue in a 6N hydrochloric acid solution to pH 1 and extract twice with 50 ml of ether each time. Dry the organic phase over magnesium sulphate and remove the ether by evaporation under reduced pressure. Crystallise the resulting oil from isopropyl ether and recrystallise the resulting precipitate from cyclohexane.

Workup

  1. customRemove the tetrahydrofuran
  2. customby evaporation under reduced pressure
  3. extractionextract twice with 50 ml of ether each time
  4. dry with materialDry the organic phase over magnesium sulphate
  5. customremove the ether
  6. customby evaporation under reduced pressure
  7. customCrystallise the resulting oil from isopropyl ether
  8. customrecrystallise the resulting precipitate from cyclohexane

Sources & evidence

ORD record
ord-6e5ad4bd5d054d9da3036ca0da32da70
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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