Triethylamine → HCID 86756768, compound

HRID 1978401Notes

Reaction equation

HRID 1978401 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1)#[N:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:13][S:14]([OH:16])(=[O:12])=[O:15].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH3:11])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110841784-(3-Hydroxypropyl)benzonitrile

Product 1

HCID 86756768HCID 86756768, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 3-(4-cyanophenyl)propanol (3.77 g, 23.4 mmol), methanesulfonylchloride (2.96 g, 25.8 mmol), triethylamine (2.60 g, 25.7 mmol) and ethyl acetate (100 ml) was stirred at room temperature for 30 minutes. Then the reaction mixture was diluted with ethyl acetate and successively washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (60 g) with hexane-ethyl acetate (1:1) to give 3-(4-cyanophenyl)propane methanesulfonate as a colorless oil (4.79 g, 86%).

Workup

  1. washsuccessively washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel (60 g) with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-810d0729c97643358c26e0af32eca4d6
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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