Triethylamine → HCID 18981012, compound

HRID 482606Notes

Reaction equation

HRID 482606 reaction equation
[OH:1][CH2:2][C:3]([O:14][CH2:15][CH2:16][CH3:17])([CH3:13])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][S:19]([O:1][CH2:2][C:3]([O:14][CH2:15][CH2:16][CH3:17])([CH3:13])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18980983HCID 18980983, compound

Product 1

HCID 18981012HCID 18981012, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To 11 g (44 mmole) of crude 2-hydroxymethyl-2-propoxy-4'-chloropropiophenone (Example 96d) in 50 ml of methylene chloride was added 4.5 g (39 mmole) of methanesulfonyl chloride. The mixture was cooled to -40° C. and then 6.0 g (60 mmole) of triethylamine was slowly added. The mixture was allowed to warm to room temperature over 1 hour and was then washed with water, dilute aqueous hydrochloric acid, and brine. It was then dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and chromatographed over silica gel using diethyl ether and hexanes to yield 5.5 g of the title compound, an oil.

Workup

  1. temperatureto warm to room temperature over 1 hour
  2. washwas then washed with water, dilute aqueous hydrochloric acid, and brine
  3. dry with materialIt was then dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed over silica gel

Sources & evidence

ORD record
ord-1c3478f6a8bb433483b2ea576f3e525d
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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