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

HRID 2075968Notes

Reaction equation

HRID 2075968 reaction equation
C([O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH:14]=1)C1C=CC=CC=1.C(Cl)Cl.Cl>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[OH:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][C:12]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)=[C:13]([C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 50899156[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanone

Product 1

HCID 136202003[5-Hydroxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl) phenyl]phenylmethanoneYield 94%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanone (reference example 14-1) (526 mg) and methylene chloride (22 mL) was added titanium(IV) chloride (0.288 mL) at room temperature. After stirring for 30 minutes, 2 mol/L hydrochloric acid and ethyl acetate were added to the mixture at room temperature. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 50%-67% ethyl acetate/hexane, gradient elution) to give the title compound (383 mg).

Workup

  1. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: 50%-67% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-d7977971a4d1416786e88d9dfed1e569
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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