Methane, dichloromethoxy- → HCID 58566765, compound

HRID 1876374Notes

Reaction equation

HRID 1876374 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, 11 mol) 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-d8a5dd6e86a249ec83c0a72f3724b641
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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