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

HRID 1297776Notes

Reaction equation

HRID 1297776 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])[C:21]([O:25][Si](C(C)(C)C)(C)C)=[C:20]([CH3:33])[CH:19]=2)([OH:17])[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])([C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([OH:25])=[C:20]([CH3:33])[CH:19]=2)[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 695228771-Benzyl-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-3-hydroxy-1,3-dihydro-indol-2-one

Product 1

HCID 695228451-Benzyl-3-hydroxy-3-(4-hydroxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-oneYield 107.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-benzyl-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-3-hydroxy-1,3-dihydro-indol-2-one (152 mg, 0.3 mmol) in THF (5 mL) and treat with 1.0M in THF tetrabutylammonium fluoride (0.36 mL, 0.36 mmol) for 6 h. Pour into ethyl acetate (25 mL) and wash with water (3×25 mL) and brine (25 mL). Dry (MgSO4), filter and concentrate in vacuo to give a summy residue. Purify by flash chromatography (gradient of 5% EtOAc/hexanes to 50% EtOAc/hexanes) to give 116 mg (98%) of the title compound as a white solid. MS (ES): m/z=376 (M+1−H2O); 1H NMR(DMSO-d6); δ8.26 (s, 1H), 7.54 (dd, J=1.7, 1.4 Hz, J=7.7, 7.4 Hz, 1H), 7.38-7.15 (m, 5H), 7.05 (t, J=7.4 Hz, 1H), 6.85 (m, 3H), 6.65 (s, 1H), 4.96 (q, 2H), 2.12 (s, 6H).

Workup

  1. washwash with water (3×25 mL) and brine (25 mL)
  2. dry with materialDry (MgSO4)
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a summy residue
  6. customPurify by flash chromatography (gradient of 5% EtOAc/hexanes to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7d30a1b75aad4d83b6926cc61e68a329
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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