Water → HCID 21451957, compound

HRID 596325Notes

Reaction equation

HRID 596325 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:25](=[O:35])[C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:25](=[O:35])[C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:1])[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54437280HCID 54437280, compound

Product 1

HCID 21451957HCID 21451957, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.5 gm (7 millimols) of ethyl 2-methyl-2-{4-[2-(2-methoxy-5-chloro-benzamido)-ethyl]-biphenyl-4'-oxy}-propionate were reduced in 30 ml of absolute ether with 0.27 gm (7 millimols) of lithium aluminum hydride. After careful addition of 8 ml of water, the mixture was filtered, the filter cake was washed first with ether and then with chloroform, the ether phase and the chloroform phase were combined with the filrate and dried over sodium sulfate. After distilling off the solvents, the residual oil was crystallized from a small quantity of ether. Yield: 1.2 gm (38% of theory); m.p. 115° C.

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake was washed first with ether
  3. dry with materialdried over sodium sulfate
  4. distillationAfter distilling off the solvents
  5. customthe residual oil was crystallized from a small quantity of ether

Sources & evidence

ORD record
ord-4394d9015f7248359de9cf2fd114ade2
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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