2,6-Dimethylphenol → 1-Benzyl-3-(3,5-dimethyl-phenyl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-one

HRID 1297763Notes

Reaction equation

HRID 1297763 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)(O)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:29]=1[OH:35]>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)([C:32]2[CH:31]=[C:30]([CH3:34])[C:29]([OH:35])=[C:28]([CH3:27])[CH:33]=2)[C:9]1=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 113352,6-DimethylphenolHCID 589146821-Benzyl-3-(3,5-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one

Product 1

HCID 589147541-Benzyl-3-(3,5-dimethyl-phenyl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-oneYield 62%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve 1-benzyl-3-(3,5-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one (68 mg, 0.2 mmol) and 2,6-dimethylphenol (122 mg, 1.0 mmol) in trifluoroacetic acid (1 mL) and stir at room temperature for 30 min. Pour the reaction over ice water and extract with ethyl acetate (2×). Wash combined organic portions with brine and then dry (Na2SO4), filter and concentrate in vacuo to give an oily residue. Purify with radial chromatography (gradient of 1 EtOAc/9 hexanes and then 1 EtOAc/5 hexanes) to give 55 mg (62%) of the title compound as a white solid. MS (ES): m/z=448 (M+1), 446 (M−1); 1H NMR(DMSO-d6): δ8.29 (s, 1H), 7.38-7.22 (m, 7H), 7.07 (m, 2H), 6.90 (s, 1H), 6.75 (s, 2H), 6.71 (s, 2H), 4.99 (s, 2H), 2.19 (s, 6H), 2.08 (s, 6H).

Workup

  1. additionPour
  2. extractionextract with ethyl acetate (2×)
  3. washWash
  4. dry with materialdry (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto give an oily residue
  8. customPurify with radial chromatography (gradient of 1 EtOAc/9 hexanes

Sources & evidence

ORD record
ord-feb45da509eb4262870df9b7e5c00057
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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