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

HRID 2075950Notes

Reaction equation

HRID 2075950 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+].Cl>C(OCC)(=O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:15])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 595656495-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 59565729[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde (reference example 15-1) (450 mg) and tetrahydrofuran (5.6 mL) was added dropwise phenylmagnesium bromide (1.08 mol/L tetrahydrofuran solution, 1.4 mL) in an ice salt bath. After stirring at the same temperature for 30 minutes, an aqueous solution of ammonium chloride, 2 mol/L hydrochloric acid and ethyl acetate were added to the mixture. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (564 mg).

Workup

  1. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84ad36e405cc4aeb9bb0758f6b56b1bc
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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