Aluminium lithium hydride → 2-Methyl-2-{4-[(2-methoxy-5-chloro-benzamido)-methyl]-biphenyl-4'-oxy}-propanol

HRID 596335Notes

Reaction equation

HRID 596335 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][NH:23][C:24](=[O:34])[C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=3[O:32][CH3:33])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>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][NH:23][C:24](=[O:34])[C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=3[O:32][CH3:33])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:1])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21418525Ethyl 2-Methyl-2-{4-[2-methoxy-5-chloro-benzamido-methyl]-biphenyl-4'-oxy}-propionate

Product 1

HCID 214519442-Methyl-2-{4-[(2-methoxy-5-chloro-benzamido)-methyl]-biphenyl-4'-oxy}-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.8 gm (3.74 millimols) of ethyl 2-methyl-2-{4-[(2-methoxy-5-chloro-benzamido)-methyl]-biphenyl-4'-oxy}-propionate were reduced to the alcohol by heating in 50 ml of ether with 0.1 gm (3.8 millimols) of lithium aluminum hydride at the boiling point of the solvent for 15 minutes. After decomposition with water, drying of the ether phase over sodium sulfate, and distilling off the ether, the alcohol was purified on a silicagel column with benzene/ethyl acetate (6:4) as the eluant. Yield: 0.5 gm (30% of theory); m.p. 109° C.

Workup

  1. dry with materialAfter decomposition with water, drying of the ether phase over sodium sulfate
  2. distillationdistilling off the ether
  3. customthe alcohol was purified on a silicagel column with benzene/ethyl acetate (6:4) as the eluant

Sources & evidence

ORD record
ord-9fc766ac7b3444d38fb9c5b3f2dc0d6b
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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