Dichloromethane → HCID 58136865, compound

HRID 657942Notes

Reaction equation

HRID 657942 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 phenyl-trimethylammonium 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-a3a57a116a5d4f8caafba889af2e3b0d
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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