Water → HCID 19820418, compound

HRID 1030464Notes

Reaction equation

HRID 1030464 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14](OC)=[O:15])=[C:4]([O:20][CH2:21][C:22]([NH:24][CH3:25])=O)[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][CH2:14][OH:15])=[C:4]([O:20][CH2:21][CH2:22][NH:24][CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54387449HCID 54387449, compound

Product 1

HCID 19820418HCID 19820418, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

27.2 g of methyl 2-[4-chloro-2-[[(methylamino) carbonyl]methoxy]phenoxy]benzeneacetate was dissolved in 800 ml of dry tetrahydrofuran and slowly added to a suspension of 8.7 g lithium aluminum hydride in 800 ml of dry tetrahydrofuran. The reaction mixture was stirred overnight at 40° C. and after addition of 35 ml of water stirred for another 1 h. The salts were removed by filtration with suction and the filtrate was evaporated in vacuo, to give 20.1 g (84%) of 2-[4-chloro-2-[2- (methylamino)ethoxy]phenoxy]benzene ethanol.

Workup

  1. stirringstirred for another 1 h
  2. customThe salts were removed by filtration with suction
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1d8d96bf2a3145d2b5ca7ca2ef13b9bc
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

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