HCID 23114134, compound → HCID 23114327, compound

HRID 1787383Notes

Reaction equation

HRID 1787383 reaction equation
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=1)[C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=2[C:6]([CH3:14])=[C:5]([NH:15][C:16](=[O:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=1[CH3:23]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:30]([C:27]1[CH:26]=[CH:25][C:24]([C:2]([C:3]2[C:11]3[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=3[C:6]([CH3:14])=[C:5]([NH:15][C:16](=[O:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=2[CH3:23])=[O:1])=[CH:29][CH:28]=1)([CH3:32])[CH3:31]

Participants

4

Reactant 1

HCID 23114134HCID 23114134, compound

Product 1

HCID 23114327HCID 23114327, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(7-(hydroxy(4-isopropylphenyl)methyl)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (209 mg, 0.48 mmol) obtained in Example 341 in dichloromethane (7 mL) was added manganese dioxide (415 mg, 4.8 mmol) and the mixture was stirred at room temperature for 8 hours. The reaction solution was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3) to obtain 156 mg (yield: 75%) of the title compound. Melting point: 194-195° C. (ethyl acetate-hexane).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-084a2665c8a94bc79cbdee373c01ca3a
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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