Hydrochloric Acid → 1-[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]-2-methylpropan-1-ol

HRID 2075951Notes

Reaction equation

HRID 2075951 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:11](I)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH:29](=[O:33])[CH:30]([CH3:32])[CH3:31].Cl>O.O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:11]([CH:29]([OH:33])[CH:30]([CH3:32])[CH3:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 508988613-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 595657261-[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]-2-methylpropan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-benzyloxy-2-iodo-5-methoxy-phenyl)-5-methyl-[1,2,4]oxadiazole (reference example 4-1) (844 mg) and tetrahydrofuran (6 mL) was cooled in an ice salt bath under an argon atmosphere. Isopropylmagnesium chloride (2.0 mol/L tetrahydrofuran solution, 1.2 mL) was added, and the mixture was stirred under ice-salt-bath cooling for 10 minutes. After an addition of isobutyraldehyde (0.55 mL), the mixture was stirred in an ice salt bath for 10 minutes, and at room temperature for 30 minutes. Water and 2 mol/L hydrochloric acid were added to the mixture, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-35% ethyl acetate/hexane, gradient elution) to give the title compound (533 mg).

Workup

  1. temperaturewas cooled in an ice salt bath under an argon atmosphere
  2. temperaturecooling for 10 minutes
  3. stirringthe mixture was stirred in an ice salt bath for 10 minutes
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: 15%-35% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-07d944356deb4676baeeb4bb98359a9d
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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