Hydrochloric Acid → HCID 2753052, compound

HRID 64455Notes

Reaction equation

HRID 64455 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C([Li])CCC.CCCCCC.Cl[C:23]([O:25][CH3:26])=[O:24].Cl>CCOCC.CC(O)C.CC(O)C.CC(O)C.CC(O)C.[Ti].C(OCC)(=O)C>[CH3:1][C:2]1([C:23]([O:25][CH3:26])=[O:24])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 130241-MethylindeneHCID 178418244HCID 178418244, compound

Product 1

HCID 2753052HCID 2753052, compound

Reagents, catalysts & solvents 3

HCID 110612Titanium tetraisopropoxideCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.4 g of 1-methyl-1H-indene in 136 ml of ether was added 16.2 ml of a 1.62 M n-butyllithium/hexane solution at −78° C., followed by stirring at room temperature for 30 minutes. To the reaction mixture were added 15.5 ml of tetra-iso-propyl titanate and 2.41 ml of methyl chloroformate at −78° C., followed by stirring at −78° C. for 2 hours. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate to carry out a layer separation operation, followed by drying over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.57 g of methyl 1-methyl-1H-indene-1-carboxylate.

Workup

  1. stirringby stirring at −78° C. for 2 hours
  2. customa layer separation operation
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4255b1769cd4469aad345cea7203b72
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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