Sodium Bicarbonate → Phthalimide

HRID 1666847Notes

Reaction equation

HRID 1666847 reaction equation
C(OC1C=C2C(=CC=1)NC=C2CC[N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])C1C=CC=CC=1.C([Si](OS(C(F)(F)F)(=O)=O)(C(C)C)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[C:21]1(=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28](=[O:29])[NH:20]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1548084HCID 1548084, compoundHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine a mixture of an oil dispersion of KH (40%, 1 g) in 30 mL anhydrous THF and a suspension of 2-(2-(5-benzyloxy-1H-indol-3-yl)ethyl)isoindole-1,3-dione (1.2 g, 3 mmol) in 30 mL THF portionwise. Stir for 1 hour at ambient temperature, cooled to 0° C., add triisopropylsilyltrifluoromethanesulfonate (1.85 g, 6 mmol) and stir an additional 1 hour at ambient temperature. Pour the reaction into a rapidly stirring solution of saturated NaHCO3 and extract with 2×50 mL EtOAc. Combine the organic layer, day over MgSO4 and concentrate to dryness and chromatograph on silica get eluting with 1% MeOH in CHCl3 to give 2-(2-5-benzyloxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione as an oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringstir an additional 1 hour at ambient temperature
  3. additionPour
  4. extractionextract with 2×50 mL EtOAc
  5. concentrationconcentrate to dryness and chromatograph on silica
  6. customget
  7. washeluting with 1% MeOH in CHCl3

Sources & evidence

ORD record
ord-e194b70f2d9943ddb03f7ac68942fbf9
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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