Sodium Sulfate → {4-[2-(Dimethylamino)ethoxy]phenyl}methanol

HRID 1808561Notes

Reaction equation

HRID 1808561 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=O)[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].[H][H]>C1COCC1.C(OCC)C>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 45792893Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10176517{4-[2-(Dimethylamino)ethoxy]phenyl}methanolYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate (for a preparation see Intermediate 19) (1.61 g, 6.79 mmol) in THF (40 mL) was cooled in ice and then treated with a 1M solution of LiAlH4 in diethyl ether (6.8 ml) and the mixture was stirred under nitrogen for 4 h. The reaction mixture was cautiously treated with saturated aq. sodium sulfate solution until the hydrogen evolution ceased. The mixture was then stirred under nitrogen for 1 h and filtered. The solid was washed with diethyl ether and the combined filtrate and washings evaporated under reduced pressure to give the title compound (1.32 g, 100%). LCMS (System B) RT=1.70 min, ES+ve m/z 196 (M+H)+.

Workup

  1. temperaturewas cooled in ice
  2. stirringThe mixture was then stirred under nitrogen for 1 h
  3. filtrationfiltered
  4. washThe solid was washed with diethyl ether
  5. customthe combined filtrate and washings evaporated under reduced pressure

Sources & evidence

ORD record
ord-1e5674945151493b8ffd5574449ded3e
Source dataset
uspto-grants-2013_01
Patent number
US08357716B2

Reaction notes

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