Sodium Hydroxide → HCID 86680888, compound

HRID 2042924Notes

Reaction equation

HRID 2042924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[C:47]1([C:50]#N)[CH2:49][CH2:48]1.[OH-:52].[Na+].CCO.[OH2:57]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[C:47]1([C:50]([OH:57])=[O:52])[CH2:49][CH2:48]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 19096565Water ethanolHCID 86680887HCID 86680887, compound

Product 1

HCID 86680888HCID 86680888, compoundYield 99%

Conditions

Temperature
110 °C

Procedure

To a solution of cyanide 42 (3.0 g, 4.25 mmol) in EtOH/H2O (20 mL/20 mL) was added NaOH (20.5 g, 423 mmol). The mixture was stirred at 110° C. for 15 hours. The mixture was cooled to room temperature and evaporated in vacuo to remove EtOH. The residue was diluted with H2O, cooled to 0° C. and acidified with c-HCl solution. The titled compound 43 was precipitated as a solid, dissolved with EtOAc and extracted. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the titled compound 43 (2.89 g, 99%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customevaporated in vacuo
  3. customto remove EtOH
  4. additionThe residue was diluted with H2O
  5. temperaturecooled to 0° C.
  6. customThe titled compound 43 was precipitated as a solid
  7. dissolutiondissolved with EtOAc
  8. extractionextracted
  9. dry with materialThe organic layer was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37031ae34b1246c6b32e3c928bc6137b
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

Loading…