Triethylamine → 4-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-methylsulfonyloxybutane

HRID 2354501Notes

Reaction equation

HRID 2354501 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[CH:10]([OH:12])[CH3:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[CH:10]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 115293394-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-butanol

Product 1

HCID 574387154-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-methylsulfonyloxybutane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanol (1.0 kg, 3.5 mol) in toluene (10 L) at 0° C. was added triethylamine (684 mL, 4.9 mol) and methanesulfonyl chloride (353 mL, 4.6 mol). After stirring for 5 min, the reaction mixture was filtered, and the precipitate was washed with toluene (8 L). The filtrate was washed with sodium bicarbonate (6 L, 50% saturated aqueous solution) and water (3 L), and concentrated to give the title compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe precipitate was washed with toluene (8 L)
  3. washThe filtrate was washed with sodium bicarbonate (6 L, 50% saturated aqueous solution) and water (3 L)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74f6c06eb2874798b603a37031b3ba0b
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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