Triethylamine → HCID 86709191, compound

HRID 1851134Notes

Reaction equation

HRID 1851134 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[CH2:3][CH3:4].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:1][CH:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([C:8]#[N:9])[CH:6]=1)[CH2:3][CH3:4])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 11435111HCID 11435111, compound

Product 1

HCID 86709191HCID 86709191, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1-hydroxypropyl)benzonitrile (0.273 g, 1.694 mmol; ref. Synlett (2002), (11), 1922-1924), Et3N (0.354 mL, 2.54 mmol) and MsCl (0.198 mL, 2.54 mmol) in CH2Cl2 (5 mL) was stirred at rt. After 90 min, an additional 0.75 eq each of Et3N and MsCl were added. After 1 h, the reaction mixture was concentrated to dryness, and the residue was partitioned between EtOAc (20 mL) and 0.1N HCl (20 mL). The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel using a 5-30% EtOAc-hexane gradient to give 1-(3-cyanophenyl)propyl methanesulfonate (0.289 g, 68% yield) (the product is somewhat unstable, and it needs to be used shortly thereafter or stored at low temperatures).

Workup

  1. waitAfter 1 h
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customthe residue was partitioned between EtOAc (20 mL) and 0.1N HCl (20 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel using a 5-30% EtOAc-hexane gradient

Sources & evidence

ORD record
ord-14bd8e2933f4431cb235d3a268ed81d4
Source dataset
uspto-grants-2015_02
Patent number
US08957104B2

Reaction notes

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