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

HRID 1248534Notes

Reaction equation

HRID 1248534 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 (400 mg) in anhydrous ether (20 ml) is added dropwise at 0°, a solution of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoate (1.2 g) in ether (10 ml). After addition is complete, the reaction mixture is stirred for about 10 minutes. Excess hydride is decomposed with wet ether and water. After filtration, the filtrate is concentrated to give the alcohol, 4-[4-(4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-penten-1-ol.

Workup

  1. additionAfter addition
  2. filtrationAfter filtration
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-569b568b9d0248ec981b6fcda116d66e
Source dataset
uspto-grants-1985_06
Patent number
US04525205

Reaction notes

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