Triethylamine → HCID 86590264, compound

HRID 1814719Notes

Reaction equation

HRID 1814719 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:15]([C:17]([OH:30])([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[CH:22][CH:21]=2)[CH3:18])=[O:16])([OH:14])[CH3:13])=[CH:7][CH:6]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>C1COCC1>[S:32]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:15]([C:17]([OH:30])([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][O:29][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:24][CH:25]=2)[CH3:18])=[O:16])([OH:14])[CH3:13])=[CH:7][CH:6]=1)([CH3:31])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18673358HCID 18673358, compound

Product 1

HCID 86590264HCID 86590264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2 °C

Procedure

A 1000 ml three-necked round bottom flask is charged with a solution of 224.26 g (1 Mol) of 4-(2-Hydroxyethoxy)phenyl 2-hydroxy-2-propyl-ketone (Darocure® 2959) in 400 mL of THF and 114.55 g (1 mol) of methanesulfonyl chloride are added to the solution at room temperature. After cooling to 2° C., 101.2 g (1 mol) of triethylamine (TEA) and 200 mL of THF are added to the solution over a 30 min-period under stirring. Slightly exothermal reaction is observed. The reaction mixture is then filtered through a G3 glass frit filter and the TEA hydrochloride washed 2× with THF on the filter. The filtrate is evaporated at 60° C./200 mbar using a Rotavapor. The resulting yellow oil is then dissolved in 800 mL of CH2Cl2. The organic phase is washed 1× with 400 mL of deionized water, 2× with 400 mL of acidic water (pH˜1) and finally with 400 mL of deionized water. The organic phase is dried over MgSO4, filtered and concentrated to constant weight by evaporating the CH2Cl2 under reduced pressure at a Rotavapor to give crude 4-(2-mesyloxyethoxy)phenyl-2-hydroxy-2-propyl-ketone.

Workup

  1. additionare added to the solution at room temperature
  2. customSlightly exothermal reaction
  3. filtrationThe reaction mixture is then filtered through a G3 glass frit
  4. filtrationfilter
  5. washthe TEA hydrochloride washed 2× with THF on the filter
  6. customThe filtrate is evaporated at 60° C./200 mbar
  7. dissolutionThe resulting yellow oil is then dissolved in 800 mL of CH2Cl2
  8. washThe organic phase is washed 1× with 400 mL of deionized water, 2× with 400 mL of acidic water (pH˜1)
  9. dry with materialThe organic phase is dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to constant weight
  12. customby evaporating the CH2Cl2 under reduced pressure at a Rotavapor

Sources & evidence

ORD record
ord-6dcba5ee8765424ba026880be2f4ebe1
Source dataset
uspto-grants-2005_04
Patent number
US06878399B2

Reaction notes

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