Ethyl cyanoformate → ethyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

HRID 859242Notes

Reaction equation

HRID 859242 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([C:25]([O:27][CH2:28][CH3:29])=[O:26])#N>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:6]2

Participants

5

Reactant 3

HCID 69336Ethyl cyanoformateHCID 787875-Methoxyindan-1-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 12177975ethyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-methoxyindan-1-one (15.0 g, 92.5 mmol) in THF (370 mL) at −78° C. was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (200 mL, 200 mmol) via an addition funnel during 15 minutes. After 40 minutes, ethyl cyanoformate (14.0 mL, 142 mmol) was added during several minutes and the reaction mixture was allowed to warm gradually. After 30 minutes, the reaction mixture was partitioned between EtOAc and dilute aqueous HCl and the organic phase was washed with water and brine and dried over Na2SO4. Filtration and removal of the solvent under reduced pressure gave ethyl 5-methoxy-1-oxoindane-2-carboxylate as a brown solid which was used in the next step without purification.

Workup

  1. temperatureto warm gradually
  2. waitAfter 30 minutes
  3. customthe reaction mixture was partitioned between EtOAc and dilute aqueous HCl
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8e4952faebe24e319f4118f7af7e91d6
Source dataset
uspto-grants-2006_12
Patent number
US07151196B2

Reaction notes

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