Water → 4-[4-(4-Trifluoromethylphenoxy)phenoxy]-pentane-1,3-diol

HRID 371025Notes

Reaction equation

HRID 371025 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:34])([F:33])[C:9]1[CH:32]=[CH:31][C:12]([O:13][C:14]2[CH:30]=[CH:29][C:17]([O:18][CH:19]([CH3:28])[C:20](=[O:27])[CH2:21][C:22](OCC)=[O:23])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.[H-].O>CCOCC>[F:7][C:8]([F:33])([F:34])[C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]2[CH:30]=[CH:29][C:17]([O:18][CH:19]([CH3:28])[CH:20]([OH:27])[CH2:21][CH2:22][OH:23])=[CH:16][CH:15]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 13469151Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 202524174-[4-(4-Trifluoromethylphenoxy)phenoxy]-pentane-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of LiAlH4 (200 mg) in anhydrous ether (15 ml) is added at 0° a solution of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate (400 mg) in ether (5 ml). After addition is complete, the reaction mixture is stirred at RT for about one hour. Excess of the hydride is decomposed using wet ether and water, the mixture is filtered and filtrate concentrated. The oily product is purified by prep. thin layer chromatography to give 4-[4-(4-trifluoromethylphenoxy)phenoxy]-pentane-1,3-diol, MS m/e 500 (M+).

Workup

  1. additionAfter addition
  2. filtrationthe mixture is filtered
  3. concentrationfiltrate concentrated
  4. customThe oily product is purified by prep

Sources & evidence

ORD record
ord-3ee71d997a3e415abad374f6aa35ea5c
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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