Methane, dichloromethoxy- → HCID 58566765, compound

HRID 2069619Notes

Reaction equation

HRID 2069619 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:4]=2[O:3]1.Cl[CH:19](Cl)[O:20]C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH2:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[C:10]([CH:19]=[O:20])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 58566660HCID 58566660, compound

Product 1

HCID 58566765HCID 58566765, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 2,2-dimethyl-5-phenyl-2,3-dihydrobenzofuran (544) (2.24 g, 10.0 mmol) in dichloromethane (15 mL) was added slowly titanium tetrachloride (2 mL, 18 mmol). After stirring of 5 minutes, dichloro(methoxy)methane (1 mL, 1 μmol) was added slowly. The resulting mixture was stirred at 0° C. for 3 hours, quenched slowly with ice water. The product was extracted with dichloromethane. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes) to provide 2,2-dimethyl-5-phenyl-2,3-dihydrobenzofuran-7-carbaldehyde (545).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 3 hours
  2. customquenched slowly with ice water
  3. extractionThe product was extracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-daf4de7dd5ce4b5b9bd2e489455bf2fd
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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