Water → 4-(4-Cyanophenyl)-4-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl methanesulfonate

HRID 411539Notes

Reaction equation

HRID 411539 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:9][CH:8]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[CH3:28][S:29]([O:1][CH2:2][CH2:3][CH2:4][CH:5]([C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)[O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:11][CH:12]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

Product 1

HCID 222355174-(4-Cyanophenyl)-4-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-{4-hydroxy-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenoxy]butyl}benzonitrile (see step (ii) above; 2.37 g, 6.45 mmol) and TEA (1.35 mL, 9.68 mmol) in DCM (10 mL) was cooled to −5° C. Methanesulfonyl chloride (0.65 mL, 8.38 mmol) in DCM (5 mL) was added slowly. After addition was complete, the temperature was maintained below 5° C. for 1 h before DCM and water were added. The organic layer was washed with water, dried (Na2SO4) and then evaporated to yield 2.87 g (100%) of the sub-title compound. This was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. additionwere added
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9b277457e9dd45738393983307b63d40
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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