Methyl 3-oxo-4-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)pentanoate → Methyl 3-hydroxy-4-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)valerate

HRID 371033Notes

Reaction equation

HRID 371033 reaction equation
[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]([CH3:23])[C:16](=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:26][C:27]([F:52])([F:51])[C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:50]=[CH:49][C:38]([O:39][CH:40]([CH3:48])[C:41](=[O:47])[CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:37][CH:36]=2)=[N:32][CH:33]=1.[BH4-].[Na+]>>[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH3:23])[CH:16]([OH:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:24][CH:25]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:51][C:27]([F:26])([F:52])[C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:50]=[CH:49][C:38]([O:39][CH:40]([CH3:48])[CH:41]([OH:47])[CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:37][CH:36]=2)=[N:32][CH:33]=1

Participants

5

Reactant 3

HCID 179795Methyl 3-oxo-4-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)pentanoateHCID 4311764Sodium borohydrideHCID 13472763HCID 13472763, compound

Product 2

HCID 179796Methyl 3-hydroxy-4-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)valerateHCID 20252431HCID 20252431, compound

Procedure

Each of the compounds, methyl 4-[4-(3,5-dichloropyridyloxy)phenoxy]-3-oxopentanoate and methyl 4-[4-(5-trifluoromethylpyridyloxy)phenoxy]-3-oxopentanoate is reacted with NaBH4 by the procedure of Example 17 to yield methyl 4-[4-(3,5-dichloropyridyloxy)phenoxy]-3-hydroxypentanoate and methyl 4-[4-(5-trifluoromethylpyridyloxy)phenoxy]-3-hydroxypentanoate, respectively.

Sources & evidence

ORD record
ord-f2f6a40120894385b76a53caec999202
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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