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

HRID 638488Notes

Reaction equation

HRID 638488 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:35])([F:34])[C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH:19]([CH3:29])[C:20]([O:27][CH3:28])=[CH:21][C:22](OCC)=[O:23])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.[H-].O>CCOCC>[F:7][C:8]([F:34])([F:35])[C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH:19]([CH3:29])[C:20]([O:27][CH3:28])=[CH:21][CH2:22][OH:23])=[CH:16][CH:15]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 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 LiAlH4 (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-62321748ea174c8ca335bdefffc03f5d
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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