5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde → 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-4-phenyl-butan-1-ol

HRID 1528907Notes

Reaction equation

HRID 1528907 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=[O:15])=[CH:4][CH:3]=1.[C:16]1([CH2:22][CH2:23][CH2:24][Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:15])[CH2:24][CH2:23][CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 665784451-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-4-phenyl-butan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to the procedure described in Example 114, Step 3, using 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde and 3-(phenyl)propylmagnesium bromide. After the reaction the material was submitted to chiral preparatory HPLC (Chiralcel AS Column, 2% EtOH in hexanes, 60 minute run). The first enantiomer off of the column is Enantiomer A.

Workup

  1. customPrepared
  2. customAfter the reaction the material

Sources & evidence

ORD record
ord-48aff62592ce48618c0001853992d8b3
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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