Aluminium lithium hydride → 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

HRID 2068231Notes

Reaction equation

HRID 2068231 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:17][CH2:16][CH2:15][C:14]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[C:13]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66852903[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 1481272-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-acetic acid ethyl ester (Example 7) was dissolved in tetrahydrofuran at room temperature under nitrogen atmosphere. Lithium aluminium hydride was added to the solution in small portions until the reaction was complete. The reaction was quenched by adding saturated ammonium chloride solution to the mixture. The product was extracted into toluene, which was dried and evaporated in vacuo. The yield 100 mg, 43%.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated ammonium chloride solution to the mixture
  3. extractionThe product was extracted into toluene, which
  4. customwas dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1eff700252b2467b9ea26d8f8eb1332b
Source dataset
uspto-grants-2012_10
Patent number
US08293947B2

Reaction notes

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