Water → 3-Methoxy-4-{4-[4-(trifluoromethyl)phenoxy]phenoxy}pent-2-en-1-ol

HRID 371024Notes

Reaction equation

HRID 371024 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:25]=[CH:24][C:11]([O:12][CH:13]([CH3:23])[C:14]([O:21][CH3:22])=[CH:15][C:16](OCC)=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[H-].O>CCOCC>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:25]=[CH:24][C:11]([O:12][CH:13]([CH3:23])[C:14]([O:21][CH3:22])=[CH:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 166653HydrideHCID 53713180HCID 53713180, compound

Product 1

HCID 537578573-Methoxy-4-{4-[4-(trifluoromethyl)phenoxy]phenoxy}pent-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of LiAIH4 (100 mg) in anhydrous ether (20 ml) is added dropwise at 0°, a solution of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoate (500 mg) in ether. After addition is complete, the reaction mixture is stirred for about 20 minutes. Excess of the hydride is decomposed using wet ether and water. Filtration and evaporation of filtrate gives the C-1 alcohol, 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-penten-1-ol, MS m/e 440 (M+).

Workup

  1. additionAfter addition
  2. filtrationFiltration and evaporation of filtrate

Sources & evidence

ORD record
ord-beca24c02c7a40c18bc5435d68cbde63
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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