N-(7-Formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide → HCID 23114244, compound

HRID 1787227Notes

Reaction equation

HRID 1787227 reaction equation
[CH2:1]([Mg]Cl)[CH3:2].[CH:5]([C:7]1[C:15]2[O:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[C:11]=2[C:10]([CH3:25])=[C:9]([NH:26][C:27](=[O:33])[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:8]=1[CH3:34])=[O:6]>O>[OH:6][CH:5]([C:7]1[C:15]2[O:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[C:11]=2[C:10]([CH3:25])=[C:9]([NH:26][C:27](=[O:33])[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:8]=1[CH3:34])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 23114128N-(7-Formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamideHCID 178461633HCID 178461633, compound

Product 1

HCID 23114244HCID 23114244, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethylmagnesium chloride (2.0 M THF solution, 5.0 mL, 10.0 mmol) was added N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (0.7 g, 1.72 mmol) obtained in Example 20 at 0° C. and the reaction solution was stirred at the same temperature for 1 hour. The reaction solution was added to water and the product was extracted with ethyl acetate. The organic layer was washed with water and 1 N hydrochloric acid, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 264 mg (yield: 35%) of the title compound as a low polarity isomer. Melting point: 145-146° C. (ethyl acetate-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water and 1 N hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e459e874028d4392ab848ad9bf488a62
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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