Ethyl Acetate → HCID 68629734, compound

HRID 2098962Notes

Reaction equation

HRID 2098962 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](C)(C)[CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH2:20]([O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33](=O)[CH2:32][CH2:31]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>C1COCC1>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33](=[CH:13][C:14]([O:16][CH3:17])=[O:15])[CH2:32][CH2:31]2)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 76210Methyl (trimethylsilyl)acetateHCID 2733832Lithium HexamethyldisilazideHCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 68629734HCID 68629734, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

At −78° C., lithium bis(trimethylsilyl)amide (1.0 M in THF) (30 mL, 30 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (5.0 mL, 30 mmol) in THF (20 mL). The reaction was maintained at −78° C. for 11 minutes and then 5-(benzyloxy)-2,3-dihydroinden-1-one (5.2) (4.0 g, 17 mmol) in 10 mL of THF was added in one portion. The resulting mixture was stirred at −78° C. and allowed to warm to room temperature overnight. EtOAc (400 mL) was added, and the mixture was washed with water and brine, and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane) to give 5.3 in 70% yield.

Workup

  1. temperatureto warm to room temperature overnight
  2. washthe mixture was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removing solvent
  5. customthe residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane)
  6. customto give 5.3 in 70% yield

Sources & evidence

ORD record
ord-eb5175dec0a1485c8f453ee132590fb6
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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