Water → HCID 10512214, compound

HRID 1722731Notes

Reaction equation

HRID 1722731 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([CH2:8][CH3:9])[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:15][N:2]([CH3:1])[C:3]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([CH2:8][CH3:9])[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10585413HCID 10585413, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10512214HCID 10512214, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-dimethylamino-2-(2-thienyl)butyrate (11.4 g) in tetrahydrofuran (50 ml) is added dropwise to a suspension of lithium aluminum hydride (1.6 g) in tetrahydrofuran (50 ml) under ice-cooling. The mixture is stirred at room temperature for 2 hours, and water (1.6 ml), an aqueous 15% sodium hydroxide solution (1.6 ml) and water (4.8 ml) are added to the mixture, successively. After the mixture is stirred, insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. The residue is distilled under reduced pressure, whereby 2-dimethylamino-2-(2-thienyl)-1-butanol (9.1 g) is obtained as colorless crystals. Yield: 91%

Workup

  1. temperaturecooling
  2. stirringAfter the mixture is stirred
  3. filtrationinsoluble materials are filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto remove solvent
  6. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-ea55868caedb4a8085c05defce347d65
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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