Potassium Hydroxide → HCID 178504545, compound

HRID 617916Notes

Reaction equation

HRID 617916 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@:20]([O:37][SiH:38]([CH3:40])[CH3:39])([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4[C:25]([CH:27]=[O:28])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-:41].[K+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@:20]([O:37][SiH:38]([CH3:40])[CH3:39])([C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4[C:25]([C:27]([OH:41])=[O:28])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 178504544HCID 178504544, compound

Product 1

HCID 178504545HCID 178504545, compoundYield 34.7%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the aldehyde from Step 2 (14 g, 24.6 mmol) in EtOH (118 mL) was added a solution of AgNO3 (10 g, 59 mmol) predissolved in H2O (23 mL) followed by a solution of KOH (118 mL, 118 mmol of 1M) dropwise. The mixture was stirred at room temperature overnight. The bulk of the EtOH was removed by evaporation, the aqueous was acidified with 1N HCl (118 mL) and extracted with EtOAc twice (100 mL). The organic extracts were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography first with pure EtOAc then using 95:5 EtOAc: AcOH, to yield 5.0 g of the title compound. 1H NMR (CD3COCD3) d 0.15 (s, 6H), 0.95 (s, 9H), 2.0 (m, 2H), 2.95-3.18 (m, 2H), 4.95 (t, 1H), 7.35-7.65 (m, 8H), 7.75-7.97 (m, 5H), 8.0 (s, 1H), 8.32 (d, 1H).

Workup

  1. customThe bulk of the EtOH was removed by evaporation
  2. extractionextracted with EtOAc twice (100 mL)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography first with pure EtOAc

Sources & evidence

ORD record
ord-80764fbce4fd47dda36c50f6059d5b6b
Source dataset
uspto-grants-1999_09
Patent number
US05952347

Reaction notes

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