Water → HCID 12070580, compound

HRID 2084746Notes

Reaction equation

HRID 2084746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([OH:11])[CH3:10].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>ClCCl>[S:20]([O:11][CH:9]([CH3:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:22])(=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 120705791-(2-Fluorophenyl)propan-2-ol

Product 1

HCID 12070580HCID 12070580, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of 2.15 g (14.0 mmol) of (+)-1-(2-fluorophenyl)-propan-2-ol and 2.34 ml (16.8 mmol) of triethylamine in 10 ml of dichloromethane, 1.19 ml (15.4 mmol) of methanesulfonyl chloride was added at 0° C. The resulting mixture was stirred overnight at room temperature and then treated with water and extracted 3 times with dichloromethane. The combined organic layer was then washed with water, solvent was distilled off and the residue was purified by silica gel chromatography, giving 2.68 g of the title compound. (Yield: 82%).

Workup

  1. additionwas added at 0° C
  2. extractionextracted 3 times with dichloromethane
  3. washThe combined organic layer was then washed with water, solvent
  4. distillationwas distilled off
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e47b25d09e4f4fbd9754053f1c07cc55
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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