Sodium Hydroxide → HCID 86722740, compound

HRID 1525796Notes

Reaction equation

HRID 1525796 reaction equation
CO[C:3](=O)[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1.[Al+3].[H-].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 131733156HCID 131733156, compound

Product 1

HCID 86722740HCID 86722740, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 7 (3.9 g) was dissolved in tetrahydrofuran (55 mL). Lithium hydride aluminum (620 mg) was carefully added thereto and the reaction solution was refluexed with heating for 2 hours. After cooling the reaction solution to room temperature, 2N aqueous sodium hydroxide solution (3 mL) was added carefully, further tetrahydrofuran and anhydrous magnesium sulfate were added, followed by stirring for 1 hour. The reaction solution was filtered with Celite (brand name) and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (3.4 g) having the following physical property values.

Workup

  1. temperaturewith heating for 2 hours
  2. filtrationThe reaction solution was filtered with Celite (brand name)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-953aa0f77e4c4217b6ae9d556cb491a6
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

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