Triethylamine → HCID 19108678, compound

HRID 1493964Notes

Reaction equation

HRID 1493964 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[O:12][CH2:13][CH2:14]O)C=CC=CC=1.C(N(CC)CC)C.S(Cl)(C)(=O)=O.[Na].[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1>C1COCC1.CO.[Pd]>[N:32]1([CH2:14][CH2:13][O:12][C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][CH:16]=2)[CH:36]=[CH:35][N:34]=[CH:33]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 121470482-(3-Benzyloxyphenoxy)ethanolHCID 57373095Imidazole sodium

Product 1

HCID 19108678HCID 19108678, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 12.2 g (0.05 mole) 2-[3-(phenylmethoxy)phenoxy]ethanol and 5.6 g (0.555 mole) of triethylamine in 100 ml of THF was cooled to 0° C. with stirring and treated dropwise with 6.4 g (0.055 mole) of mesyl chloride over a 20-min period. The mixture was stirred at 10° C. or less for 1 hr, then filtered. The filtrate was combined with a slurry of 0.10 mole of imidazole sodium salt in 50 ml of THF and the mixture was heated at reflux for 8 hr. The 50 ml of THF and the mixture was heated at reflux for 8 hr. The cooled reaction mixture was filtered and the filtrate was partitioned between ethyl acetate/ether and water. The organic layer was concentrated to give 14.7 g (100%) of crude intermediate. This syrup (13.0 g) was dissolved in 100 ml of methanol and hydrogenated at 40° C. and 45 psi H2 using 1 g of 10% Pd/C catalyst. This mixture was filtered, and the filtrate was concentrated to give 9.0 g (100%) of crude, crystalline product. A portion was recrystallized from toluene/methyl isobutyl ketone to give the title compound as white crystals, mp 125.0° C.-127.0° C.

Workup

  1. stirringThe mixture was stirred at 10° C. or less for 1 hr
  2. filtrationfiltered
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 8 hr
  5. temperatureat reflux for 8 hr
  6. customThe cooled reaction mixture
  7. filtrationwas filtered
  8. customthe filtrate was partitioned between ethyl acetate/ether and water
  9. concentrationThe organic layer was concentrated
  10. customto give 14.7 g (100%) of crude intermediate
  11. filtrationThis mixture was filtered
  12. concentrationthe filtrate was concentrated
  13. customto give 9.0 g (100%) of crude, crystalline product
  14. customA portion was recrystallized from toluene/methyl isobutyl ketone

Sources & evidence

ORD record
ord-58fd311654654d11a46a8dadd6862b16
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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