Diethyl Ether → 3-Hydroxy-3-phenyl-1,3-dihydroindol-2-one

HRID 1297759Notes

Reaction equation

HRID 1297759 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C1COCC1>[OH:5][C:4]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7054IsatinHCID 178418255HCID 178418255, compound

Product 1

HCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve isatin (1.47 g, 10 mmol) in anhydrous THF (40 mL) in an oven-dried flask under nitrogen. Cool in an ice bath and add slowly a 3M solution of phenylmagnesium bromide in diethyl ether (7.4 mL, 22 mmol). After 5 min remove the ice bath and stir at room temperature for 18 h. Pour the reaction over saturated NH4Cl solution and extract with ethyl acetate (200 mL, 2×100 mL). Wash combined organic portions with brine and dry (Na2SO4), filter, and concentrate in vacuo to give a yellow solid. Triturate in diethyl ether, filter and dry under house vacuum to give 1.77 g (79%) of the title compound as a yellow solid. MS (ES): m/z=208 (M+1−H2O), 224 (M−1); 1H NMR(DMSO-d6): δ10.39 (s, 1H), 7.32-7.23 (m, 6H), 7.09 (d, J=7.3 Hz, 1H), 6.96 (dt, J=0.9 Hz, J=7.5 Hz, 1H), 6.90 (d, J=7.7 Hz, 1H), 6.61 (s, 1H).

Workup

  1. temperatureCool in an ice bath
  2. customAfter 5 min remove the ice bath
  3. additionPour
  4. customthe reaction over saturated NH4Cl solution
  5. extractionextract with ethyl acetate (200 mL, 2×100 mL)
  6. washWash
  7. dry with materialdry (Na2SO4)
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto give a yellow solid
  11. customTriturate in diethyl ether
  12. filtrationfilter
  13. customdry under house vacuum

Sources & evidence

ORD record
ord-c73a153355c74afb92fc38dff8ad6684
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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