Sodium Hydroxide → HCID 178509872, compound

HRID 1969506Notes

Reaction equation

HRID 1969506 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C@@H:9]2[CH2:12][C@H:11]([C:13]([O:15]CC)=[O:14])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@@H:9]2[CH2:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10]2)=[CH:18][CH:19]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472523HCID 178472523, compound

Product 1

HCID 178509872HCID 178509872, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of cis-ethyl 3-(4-cyanobenzyloxy)cyclobutanecarboxylate (0.44 g, 1.70 mmol) in 1,4-dioxane (10 mL) was added aqueous NaOH (1 N, 2.0 mL). The reaction was stirred at about 25° C. for about 16 h. The reaction was partitioned between 10% aqueous AcOH (20 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer was extracted with additional EtOAc (25 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered then concd in vacuo to give cis-3-(4-cyanobenzyloxy)-cyclobutanecarboxylic acid (0.24 g, 60%): LC/MS (Table 1, Method b) Rt=1.67 min; MS m/z: 232 (M+H)+.

Workup

  1. customThe reaction was partitioned between 10% aqueous AcOH (20 mL) and EtOAc (25 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional EtOAc (25 mL)
  4. washThe combined organic extracts were washed with brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ed821eb710b0435ab4ec649b864e98f1
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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