Dichloromethane → HCID 58136865, compound

HRID 1524535Notes

Reaction equation

HRID 1524535 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:22](=[O:24])[CH3:23])[CH:8]=[C:9]([CH2:11][O:12][CH2:13][CH2:14][O:15]C2CCCCO2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C(Cl)[Cl:59]>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:22](=[O:24])[CH2:23][Cl:59])[CH:8]=[C:9]([CH2:11][O:12][CH2:13][CH2:14][OH:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58045872HCID 58045872, compound

Product 1

HCID 58136865HCID 58136865, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-{3-tert-Butyl-5-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]phenyl}ethanone (O2.063; 2.0 g) was dissolved in methanol/THF (30 ml/30 ml) and admixed while stirring with phenyltrimethylammonium tribromide (2.25 g). After stirring at RT for 3 h, the mixture was diluted with DCM and washed once with 5% sodium thiosulfate solution, and the DCM phase was dried over magnesium sulfate and concentrated by rotary evaporation. The residue was dissolved in THF (200 ml), and 3 N HCl (30 ml) was added. After standing for 1 h, EA and water were added, and the EA phase was removed. The EA phase was dried over magnesium sulfate and concentrated by rotary evaporation. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 40 min). 774 mg of the title compound were obtained.

Workup

  1. washwashed once with 5% sodium thiosulfate solution
  2. dry with materialthe DCM phase was dried over magnesium sulfate
  3. concentrationconcentrated by rotary evaporation
  4. dissolutionThe residue was dissolved in THF (200 ml)
  5. addition3 N HCl (30 ml) was added
  6. waitAfter standing for 1 h
  7. additionEA and water were added
  8. customthe EA phase was removed
  9. dry with materialThe EA phase was dried over magnesium sulfate
  10. concentrationconcentrated by rotary evaporation
  11. customThe residue was purified
  12. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 40 min)

Sources & evidence

ORD record
ord-b1e8dc73b3b44f79953d7c9ca6386b18
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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