7-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one → 3-(4-Chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-one

HRID 14466Notes

Reaction equation

HRID 14466 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[C:17]2[C:12]([C:13](=[O:31])[C:14]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[C:15]([CH:21]([CH3:23])[CH3:22])[O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>O1CCCC1.C(O)C.Cl.[Pd].[C]>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:14]2[C:13](=[O:31])[C:12]3[C:17](=[C:18]([O:19][CH3:20])[C:9]([OH:8])=[CH:10][CH:11]=3)[O:16][C:15]=2[CH:21]([CH3:23])[CH3:22])=[CH:29][CH:28]=1

Participants

6

Reactant 1

HCID 687032587-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one

Product 1

HCID 116026403-(4-Chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-one

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 7-benzyloxy-3-(4-chlorophenyl)-2-isopropyl-8-methoxy-chromen-4-one (2.68 g, 6.16 mmol) and Pd/carbon (20%, 268 mg) in tetrahydrofuran (30 ml), absolute ethanol (30 ml) and 5M HCl solution (15 ml) is stirred under a balloon of H2 at room temperature for 3 h. The reaction mixture is filtered through a pad of Celite filter aid, which is itself washed with tetrahydrofuran. The solvent is removed under reduced pressure to afford the desired product, which is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. filtrationfilter aid, which
  3. washwashed with tetrahydrofuran
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f6ceb956a24d4e769e39b92cd6f2fd8c
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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