Triethylamine → 3,3-Diphenylpropyl methanesulfonate

HRID 2228665Notes

Reaction equation

HRID 2228665 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>O1CCCC1.O>[CH3:17][S:18]([O:10][CH2:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 299083,3-DiphenylpropanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 222382923,3-Diphenylpropyl methanesulfonateYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 3,3-diphenyl-1-propanol (24.0 g, 113 mmol) and methanesulfonyl chloride (13.7 g, 120 mmol) in tetrahydrofuran (200 mL) was added triethylamine (17.0 mL, 120 mmol) gradually at 0° C. and the mixture was stirred at room temperature for 10 minutes. This reaction mixture was diluted with water (200 mL) and extracted with 2 portions of ethyl acetate. The combined organic solution was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from diisopropyl ether to provide 25.8 g of the title compound. Yield 79%.

Workup

  1. extractionextracted with 2 portions of ethyl acetate
  2. washThe combined organic solution was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ea687d578af346799e471d40886c31da
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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