Water → 4-(4-Cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate

HRID 500476Notes

Reaction equation

HRID 500476 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[O:11][CH:12]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[CH2:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([O:16][CH2:15][CH2:14][CH2:13][CH:12]([C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[O:11][C:10]1[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:8]([O:7][CH3:6])[CH:9]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 218677264-[1-(3,4-Dimethoxyphenoxy)-4-hydroxybutyl]benzonitrile

Product 1

HCID 218675684-(4-Cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (3.4 mL, 5.0 g, 44 mmol) in DCM (15 mL) was added slowly to a cooled (−5° C.) mixture of 4-[1-(3,4-dimethoxyphenoxy)-4-hydroxybutyl]benzonitrile (from step (ii) above; 11 g, 34 mmol) and triethylamine (7 mL, 5.2 g, 50.6 mmol) in DCM (50 mL), during which addition the temperature did not rise above 2° C. Stirring was continued at between 0 and 5° C. for a further 2 h before water was added. The resulting organic layer was separated, and washed with water, separated again and then dried to give the sub-title compound in 100% yield.

Workup

  1. temperaturea cooled
  2. customdid not rise above 2° C
  3. additionwas added
  4. customThe resulting organic layer was separated
  5. washwashed with water
  6. customseparated again
  7. customdried

Sources & evidence

ORD record
ord-31bd80d509f0402dbc39df326cc7740c
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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