Hydrochloric Acid → HCID 15298916, compound

HRID 333328Notes

Reaction equation

HRID 333328 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C:8]1([C:17]([O:19]C)=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(Cl)Cl.Cl>CCO.C1COCC1>[C:1]([O:5][C:6](=[O:21])[CH2:7][C:8]1([C:17]([OH:19])=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 15298915HCID 15298915, compound

Product 1

HCID 15298916HCID 15298916, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 2-(2-tert-butoxy-2-oxoethyl)-2,3-dihydro-1H-indene-2-carboxylate (4.5 g, 15.50 mmol) in EtOH/THF (70 mL, 1:1) at room temperature was added 1 M sodium hydroxide (35 ml, 35.0 mmol), and the mixture was stirred at room temperature for 1.5 hour. To the reaction mixture was added DCM and acidified by 1 M HCl to pH=7. The mixture was extracted with DCM, and the combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 10 to 30% EtOAc/HEP) and gave the title compound: 1.4 g (yield: 15%). LCMS (condition B): 275.2 (M−1); retention time=1.17 min.

Workup

  1. extractionThe mixture was extracted with DCM
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by flash chromatography (silica gel, 10 to 30% EtOAc/HEP)

Sources & evidence

ORD record
ord-9823ddc285494652879826281cd8f510
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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