Aluminium lithium hydride → 2-{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-ethanol

HRID 1785583Notes

Reaction equation

HRID 1785583 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19][Cl:20])=[CH:12][CH:11]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:20][CH2:19][CH2:18][C:17]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[C:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][OH:3])=[CH:15][CH:14]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69038968{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-acetic acid ethyl ester

Product 1

HCID 668520532-{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-ethanolYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-acetic acid ethyl ester was dissolved in tetrahydrofuran at room temperature under nitrogen atmosphere. Lithium aluminium hydride was added to the solution in small portions until the reduction reaction was complete. The reaction was quenched with saturated aqueous ammonium chloride solution. The product was extracted into toluene, which was dried and evaporated in vacuo. The residue was purified with flash chromatography with toluene/triethyl amine (9.5:0.5) as eluent. Yield 68%.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  2. extractionThe product was extracted into toluene, which
  3. customwas dried
  4. customevaporated in vacuo
  5. customThe residue was purified with flash chromatography with toluene/triethyl amine (9.5:0.5) as eluent

Sources & evidence

ORD record
ord-c273e1961db040fcb48a169d3d35292e
Source dataset
uspto-grants-2009_03
Patent number
US07504530B2

Reaction notes

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